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[ CAS No. 53774-20-2 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 53774-20-2
Chemical Structure| 53774-20-2
Chemical Structure| 53774-20-2
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Product Details of [ 53774-20-2 ]

CAS No. :53774-20-2 MDL No. :MFCD00042650
Formula : C5H8O2 Boiling Point : -
Linear Structure Formula :HO2CCH2CHCHCH3 InChI Key :GQWNPIKWYPQUPI-UHFFFAOYSA-N
M.W : 100.12 Pubchem ID :143088
Synonyms :

Calculated chemistry of [ 53774-20-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 7
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.4
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 27.45
TPSA : 37.3 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.12 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.22
Log Po/w (XLOGP3) : 1.11
Log Po/w (WLOGP) : 0.89
Log Po/w (MLOGP) : 0.79
Log Po/w (SILICOS-IT) : 0.34
Consensus Log Po/w : 0.87

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -1.03
Solubility : 9.39 mg/ml ; 0.0938 mol/l
Class : Very soluble
Log S (Ali) : -1.49
Solubility : 3.27 mg/ml ; 0.0326 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.06
Solubility : 87.8 mg/ml ; 0.877 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.05

Safety of [ 53774-20-2 ]

Signal Word:Danger Class:8
Precautionary Statements:P210-P234-P260-P264-P280-P301+P330+P331+P310-P303+P361+P353+P310+P363-P304+P340+P310-P305+P351+P338+P310-P370+P378-P390-P403+P235-P405-P406-P501 UN#:3265
Hazard Statements:H227-H290-H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 53774-20-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 53774-20-2 ]

[ 53774-20-2 ] Synthesis Path-Downstream   1~97

  • 1
  • [ 106-98-9 ]
  • [ 1822-71-5 ]
  • [ 53774-20-2 ]
YieldReaction ConditionsOperation in experiment
With pentane
  • 2
  • (E/Z)-crotyl bromide [ No CAS ]
  • [ 22037-73-6 ]
  • [ 53774-20-2 ]
YieldReaction ConditionsOperation in experiment
With diethyl ether; magnesium
  • 3
  • [ 107-01-7 ]
  • [ 1822-71-5 ]
  • [ 53774-20-2 ]
YieldReaction ConditionsOperation in experiment
With pentane
  • 4
  • (E/Z)-crotyl bromide [ No CAS ]
  • [ 124-38-9 ]
  • [ 53774-20-2 ]
YieldReaction ConditionsOperation in experiment
58% Stage #1: (E/Z)-crotyl bromide With lithium chloride; zinc In tetrahydrofuran for 2h; Stage #2: carbon dioxide With hydrogenchloride for 24h;
(i) Mg, (ii) /BRN= 1900390/; Multistep reaction;
Stage #1: (E/Z)-crotyl bromide; carbon dioxide With indium; cesium fluoride In N,N-dimethyl-formamide at 60℃; for 14h; Autoclave; Stage #2: With hydrogenchloride; water In ethyl acetate; N,N-dimethyl-formamide regioselective reaction;
  • 5
  • [ 563-52-0 ]
  • [ 124-38-9 ]
  • [ 53774-20-2 ]
YieldReaction ConditionsOperation in experiment
70% Stage #1: 2-chloro-3-butene With iodine; magnesium In tetrahydrofuran Inert atmosphere; Reflux; Stage #2: carbon dioxide In tetrahydrofuran at -78℃; for 1h; Inert atmosphere;
(i) Mg, (ii) /BRN= 1900390/; Multistep reaction;
With magnesium Multistep reaction;
Stage #1: 2-chloro-3-butene With magnesium In tetrahydrofuran Heating; Stage #2: carbon dioxide In tetrahydrofuran at -78 - 10℃; Further stages.;
19 %Spectr. Stage #1: 2-chloro-3-butene; carbon dioxide With indium; lithium iodide In N,N-dimethyl-formamide at 60℃; for 14h; Autoclave; Stage #2: With hydrogenchloride; water In ethyl acetate; N,N-dimethyl-formamide regioselective reaction;

  • 6
  • [ 53774-20-2 ]
  • [ 4516-90-9 ]
YieldReaction ConditionsOperation in experiment
84% With lithium aluminium tetrahydride
75% With lithium aluminium tetrahydride In diethyl ether Heating;
With lithium aluminium tetrahydride
  • 7
  • [ 53774-20-2 ]
  • [ 24560-24-5 ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride
With oxalyl dichloride at 0 - 20℃; for 57h;
With oxalyl dichloride In chloroform at 0 - 20℃; for 3h;
With 1-chloro-1-(dimethylamino)-2-methyl-1-propene In dichloromethane at 20℃; for 1h;
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere;

  • 8
  • [ 53774-20-2 ]
  • [ 59014-11-8 ]
YieldReaction ConditionsOperation in experiment
18.5% With (R)-1-phenyl-ethyl-amine In acetone Inert atmosphere; Reflux; (S)-2-Methyl-3-butenoic acid ((S)-4; Method A) To a stirring solution of (±)-2-methyl-3-butenoic acid ((±)-4, 20.0 g, 0.200 mol) in acetone (200 mL) was added (R)-1-phenylethylamine (24.2 g, 0.200 mol) dropwise. The mixture washeated under reux to dissolve a precipitated salt. After coolingto room temperature, the precipitated salt was ltered. The resultingsalt was puried by recrystallization (1.0 g of salt/4.5 mLof acetone, twice). The obtained salt (9.07 g) was dissolved intodil. HCl (3 ; 90 mL), and the solution was extracted with Et2O.The organic layer was washed with brine, dried (Na2SO4) andconcentrated under reduced pressure to give (S)-4 (3.69 g, 18.5%yield): []D23 = +23.0 (c 1.50, CHCl3); NMR H (300 MHz, CDCl3):1.30 (3H, d, J = 7.2 Hz), 3.19 (1H, quint, J = 7.2 Hz), 5.14 (1H, dt,J = 10.2, 1.2 Hz), 5.18 (1H, dt, J = 17.1, 1.2 Hz), 5.93 (1H, ddd, J = 17.1,10.2, 7.2 Hz), 10.18 (1H, br); NMR C (125 MHz, CDCl3): 16.5, 43.5,116.6, 136.5, 181.2. The enantiomeric purity of (S)-4 was determinedby chiral GC analysis to be 54% e.e. Chiral GC: conditions:column, Chiramix (Tamogami et al. 2001) (0.25mmID × 30mL,0.25 μm df); temperature, 75 °C to 180 °C (0.7 °C/min); carrier N2(0.7 mL/min); tR (S)-4: 31.0 min (77.0%), (R)-4: 32.1 min (23.0%).
With (-)-α-methylbenzylamine
  • 9
  • [ 80-59-1 ]
  • [ 53774-20-2 ]
YieldReaction ConditionsOperation in experiment
83% With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78 - 20℃; for 1h; Inert atmosphere;
82.9% With lithium diisopropyl amide In tetrahydrofuran; hexane for 1h; Ambient temperature;
With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78 - 24℃; for 1h;
  • 10
  • [ 53774-20-2 ]
  • [ 16644-98-7 ]
  • (3S,5S)-5-((E)-Hex-1-enyl)-3-methyl-dihydro-furan-2-one [ No CAS ]
  • (3R,5S)-5-((E)-Hex-1-enyl)-3-methyl-dihydro-furan-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N,N-diethyl-N-isopropylamine; tetrabutyl-ammonium chloride In N,N-dimethyl-formamide at 80℃; for 20h; Yield given. Yields of byproduct given;
  • 11
  • [ 53774-20-2 ]
  • [ 3240-34-4 ]
  • dihydro-3-methyl-4-acetoxy-2(3H)-furanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
51% With tetrafluoroboric acid In acetic acid for 1h; Ambient temperature;
  • 12
  • [ 53774-20-2 ]
  • [ 588-72-7 ]
  • (3S,5S)-3-Methyl-5-((E)-styryl)-dihydro-furan-2-one [ No CAS ]
  • (3R,5S)-3-Methyl-5-((E)-styryl)-dihydro-furan-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N,N-diethyl-N-isopropylamine; tetrabutyl-ammonium chloride In N,N-dimethyl-formamide at 80℃; for 20h; Yield given. Yields of byproduct given;
  • 13
  • [ 53774-20-2 ]
  • 4-Bromomethyl-3-methyl-oxetan-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
42% With bromine; sodium hydrogencarbonate at 0℃;
  • 14
  • [ 53774-20-2 ]
  • [ 64-19-7 ]
  • cis-dihydro-3-methyl-4-acetoxy-2(3H)-furanone [ No CAS ]
  • trans-dihydro-3-methyl-4-acetoxy-2(3H)-furanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 37% 2: 37% With ammonium persulfate; trifluorormethanesulfonic acid at 70℃;
  • 15
  • [ 53774-20-2 ]
  • [ 106-99-0 ]
  • (3E,6E)-2-Methyl-octa-3,6-dienoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% at 120℃; for 14h;
  • 16
  • [ 124-38-9 ]
  • [ 106-99-0 ]
  • [ 53774-20-2 ]
YieldReaction ConditionsOperation in experiment
70% With isopropylmagnesium bromide In diethyl ether Ambient temperature;
  • 17
  • [ 124-38-9 ]
  • [ 591-97-9 ]
  • [ 53774-20-2 ]
YieldReaction ConditionsOperation in experiment
With magnesium 1.) -70 deg C, THF; 2.) -70 deg C, 0.5 h, then allowed to warm up to 0 deg C; Yield given. Multistep reaction;
49 %Spectr. Stage #1: carbon dioxide; 1-chloro-2-butene With indium; lithium iodide In N,N-dimethyl-formamide at 60℃; for 14h; Autoclave; Stage #2: With hydrogenchloride; water In ethyl acetate; N,N-dimethyl-formamide regioselective reaction;
  • 18
  • (E)-1-Bromo-2-butene [ No CAS ]
  • [ 124-38-9 ]
  • [ 1617-32-9 ]
  • [ 53774-20-2 ]
YieldReaction ConditionsOperation in experiment
1: 28 % Spectr. 2: 72 % Spectr. With tetraethylammonium perchlorate; magnesium In N,N-dimethyl-formamide at -10℃; electrochemical reaction;
  • 19
  • [ 53774-20-2 ]
  • [ 3282-30-2 ]
  • C10H16O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In tetrahydrofuran at -78℃; for 1h;
  • 20
  • [ 53774-20-2 ]
  • [ 543-27-1 ]
  • C10H16O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 4-methyl-morpholine In tetrahydrofuran at -78℃; for 1h;
With 4-methyl-morpholine In tetrahydrofuran for 0.0833333h;
  • 21
  • [ 75-77-4 ]
  • [ 53774-20-2 ]
  • (E)-2-Methyl-4-trimethylsilanyl-but-2-enoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
51% With n-butyllithium; potassium <i>tert</i>-butylate In tetrahydrofuran; hexane at -75℃;
  • 22
  • [ 53774-20-2 ]
  • [ 22122-36-7 ]
YieldReaction ConditionsOperation in experiment
With bromine; triethylamine 1.) CH2Cl2, 1 h, 2.) CHCl3, reflux, 4 h; Yield given. Multistep reaction;
Multi-step reaction with 2 steps 1: 42 percent / Br2, NaHCO3 / 0 °C 2: 59 percent / AgNO3 / acetic acid / Heating
  • 23
  • [ 80-59-1 ]
  • [ 591-51-5 ]
  • [ 53774-20-2 ]
  • [ 19731-91-0 ]
YieldReaction ConditionsOperation in experiment
43% In tetrahydrofuran at -30℃; for 5h;
YieldReaction ConditionsOperation in experiment
68% With water In diethyl ether Ambient temperature;
  • 25
  • [ 53774-20-2 ]
  • [ 107-18-6 ]
  • 2-methyl-but-3-enoic acid allyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With toluene-4-sulfonic acid In chloroform for 16h; Heating;
  • 26
  • [ 53774-20-2 ]
  • [ 513-42-8 ]
  • 2-methyl-but-3-enoic acid 2-methyl-allyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With toluene-4-sulfonic acid In chloroform for 16h; Heating;
  • 27
  • [ 124-38-9 ]
  • [ 17486-12-3 ]
  • [ 53774-20-2 ]
YieldReaction ConditionsOperation in experiment
42% With methylaluminum dichloride In hexane at 20℃; for 3h;
  • 28
  • [ 124-38-9 ]
  • [ 34584-84-4 ]
  • [ 53774-20-2 ]
YieldReaction ConditionsOperation in experiment
43% With methylaluminum dichloride In hexane at 20℃; for 3h;
  • 29
  • [ 16529-56-9 ]
  • [ 53774-20-2 ]
YieldReaction ConditionsOperation in experiment
100 % Chromat. With potassium phosphate buffer; Escherichia coli SS1001 cells In water at 35℃; for 1h;
With water at 35℃; for 1h; Enzymatic reaction; potassium phosphate buffer; 18 EXAMPLE; 18 Hydrolysis of 2-Methyl-3-Butenitrile to 2-Methyl-3-Butenoic acid by E. coli SS1001 Cells A 5.0 mL suspension of 0.500 g (wet cell paste) E. COLI SS1001 cells (ATCC PTA-1177) in 50 mM potassium phosphate buffer (pH 7.0) was added to a mixture of 4.91 mL of 50 mM potassium phosphate buffer (PH 7.0) and 81.8 mg of 2-methyl-3-butenenitrile (101 mM final concentration), and the resulting suspension stirred at 35 C. Samples (0.100 mL) were mixed with 0.900 mL of 60 mM N-ethylacetamide (HPLC external standard) in 1: 1 ACETONITRILE : methanol, the resulting mixture was mixed, centrifuged, and the supernatant analyzed by HPLC for 2-METHYL- 3-butenenitrile and 2-methyl-3-butenoic acid. After 1 H, the conversion of 2-methyl-3-butenenitrile was 100 %, and 2-methyl-3-butenoic acid was the only product produced over the course of the reaction.
  • 30
  • [ 53774-20-2 ]
  • [ 125763-07-7 ]
  • (3R,4R)-4-Bromomethyl-3-methyl-oxetan-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-Bromosuccinimide; diphenyl diselenide In acetonitrile at -30℃; for 5h; Title compound not separated from byproducts;
With bromine; sodium hydrogencarbonate In diethyl ether
  • 31
  • acetic acid 1-ethoxythiocarbonylsulfanyl-3-methyl-butyl ester [ No CAS ]
  • [ 53774-20-2 ]
  • 5-acetoxy-3-ethoxythiocarbonylsulfanyl-2,7-dimethyl-octanoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With dilauryl peroxide In 1,2-dichloro-ethane Heating;
  • 32
  • [ 4894-61-5 ]
  • [ 124-38-9 ]
  • [ 53774-20-2 ]
YieldReaction ConditionsOperation in experiment
55% Stage #1: trans-but-2-enyl chloride With iodine; magnesium In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; Reflux; Stage #2: carbon dioxide With sulfuric acid In tetrahydrofuran at -78℃; for 0.5h;
51% Stage #1: trans-but-2-enyl chloride With magnesium In tetrahydrofuran for 3h; Heating; Stage #2: carbon dioxide In tetrahydrofuran Further stages.;
  • 33
  • [ 53774-20-2 ]
  • [ 100-51-6 ]
  • [ 37526-85-5 ]
YieldReaction ConditionsOperation in experiment
98% With dmap; dicyclohexyl-carbodiimide at 20℃; for 12h;
98% With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 4h; 116.116B To a solution of 2-methylbut-3-enoic acid (2 g, 18.98 mmol) in CH2C12 (38.0 ml) was added phenylmethanol (1.966 ml, 18.98 mmol), DCC (3.92 g, 18.98 mmol) and DMAP (0.232 g, 1.898 mmol) (slight exotherm). The reaction was stirred at rt for four hours. The reaction was filtered off solid, rinsed with hexane, concentrated. Purification by normal phase chromatography gave 3.55 g (98%) of 116B as a colorless oil
95% With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 16h; 2.1 To a solution of 2-methylbut-3-enoic acid (1.0 g, 9.99 mmol) in dichloromethane (1 mL) was added benzyl alcohol (1.1 g, 9.99 mmol), N,N-dicyclohexylcarbodiimide (2.1 g, 9.99 mmol) and dimethylaminopyridine (122 mg, 1.00 mmol). After stirring at 20 °C for 16 hours, the reaction mixture was filtered. The filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, 100 - 200 mesh, 0 - 5% ethyl acetate in petroleum ether) to afford benzyl 2-methylbut-3-enoate (1.8 g, 95%) as colorless oil.
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; Inert atmosphere;
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Intermediate 13. Benzyl 2-methylbut-3-enoate: To a solution of 2-methylbut- 3-enoic acid (9.5 g, 95 mmol) in DCM (80 mL) was added phenylmethanol (10.26 g, 95 mmol), N^-methanediylidenedicyclohexanamine (19.58 g, 95 mmol) and DMAP (1.159 g, 9.49 mmol) (exothermic reaction) and the resulting mixture was stirred at rt over weekend. The reaction mixture was filtered through a pad of CELITE to remove the solids and the filtrate was collected and concentrated. The filtrate was then concentrated and subjected to silica gel chromatography to yield the desired product as colorless oil.
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; [00354] Intermediate 17. Benzyl 2-methylbut-3-enoate: To a solution of 2-methylbut- 3-enoic acid (9.5 g, 95 mmol) in DCM (80 mL) was added phenylmethanol (10.26 g, 95 mmol), N^-methanediylidenedicyclohexanamine (19.58 g, 95 mmol) and DMAP (1.159 g, 9.49 mmol) (exothermic reaction) and the reaction was stirred at rt over weekend. The reaction mixture was filtered through a pad of CELITE to remove the solids and the filtrate was concentrated. The residue was purified by silica gel chromatography to yield the desired product as a colorless oil.
186.2 mg With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Cooling with ice;

  • 34
  • [ 53774-20-2 ]
  • furan-2-yl-(2-methyl-but-3-enoyl)-carbamic acid <i>tert</i>-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 4-methylmorpholine / tetrahydrofuran / 0.08 h 2: 0.69 g / n-BuLi / tetrahydrofuran; hexane / 0.17 h / 0 °C
  • 35
  • [ 53774-20-2 ]
  • tert-butyl 4-methyl-3-oxo-10-oxa-2-azatricyclo[5.2.101,5]dec-8-ene-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 4-methylmorpholine / tetrahydrofuran / 0.08 h 2: 0.69 g / n-BuLi / tetrahydrofuran; hexane / 0.17 h / 0 °C 3: 96 percent / 12 h / 25 °C
  • 36
  • [ 53774-20-2 ]
  • tert-butyl 4-methyl-3-oxo-10-oxa-2-azatricyclo[5.2.101,5]dec-8-ene-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 4-methylmorpholine / tetrahydrofuran / 0.08 h 2: 0.69 g / n-BuLi / tetrahydrofuran; hexane / 0.17 h / 0 °C 3: 12 h / 25 °C
  • 37
  • [ 53774-20-2 ]
  • [ 343268-71-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 72 percent / p-TsOH / CHCl3 / 16 h / Heating 2: 75 percent / Ti(OiPr)4 / RuCl2(=CHPh)(PCy3)(1,3-Mes-2-imidazolidin-2-yl) / 7.5 h / Heating
  • 38
  • [ 53774-20-2 ]
  • 3-methyl-3,6-dihydro-pyran-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 75 percent / p-TsOH / CHCl3 / 16 h / Heating 2: 83 percent / Ti(OiPr)4 / RuCl2(=CHPh)(PCy3)(1,3-Mes-2-imidazolidin-2-yl) / 7.5 h / Heating
  • 39
  • [ 53774-20-2 ]
  • (4R,5S,2'R)-3-(2'-methyl-3'-butenoyl)-4-methyl-5-phenyl-2-oxazolidinone [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-methylmorpholine / tetrahydrofuran / 1 h / -78 °C 2: 1.) n-BuLi, 2.) N-methylmorpholine / 1.) THF, -78 deg C, 2.) THF, a) -78 deg C, 1 h, b) RT, 4 h
Multi-step reaction with 2 steps 1: N-methylmorpholine / tetrahydrofuran / 1 h / -78 °C 2: 1.) n-BuLi / 1.) THF, -78 deg C, 30 min, 2.) THF, a) -78 deg C, 1 h, b) from -78 deg C to RT, 4 h
  • 40
  • [ 53774-20-2 ]
  • (4R,5S,2'S)-3-(2'-methyl-3'-butenoyl)-4-methyl-5-phenyl-2-oxazolidinone [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-methylmorpholine / tetrahydrofuran / 1 h / -78 °C 2: 1.) n-BuLi, 2.) N-methylmorpholine / 1.) THF, -78 deg C, 2.) THF, a) -78 deg C, 1 h, b) RT, 4 h
Multi-step reaction with 2 steps 1: N-methylmorpholine / tetrahydrofuran / 1 h / -78 °C 2: 1.) n-BuLi / 1.) THF, -78 deg C, 30 min, 2.) THF, a) -78 deg C, 1 h, b) from -78 deg C to RT, 4 h
  • 41
  • [ 53774-20-2 ]
  • (S)-4-Benzyl-3-((R)-2-methyl-but-3-enoyl)-oxazolidin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Et3N / tetrahydrofuran / 1 h / -78 °C 2: 1.) n-BuLi, 2.) Et3N / 1.) THF, -78 deg C, 2.) THF, a) -78 deg C, 1 h, b) RT, 4 h
Multi-step reaction with 2 steps 1: Et3N / tetrahydrofuran / 1 h / -78 °C 2: 1.) n-BuLi / 1.) THF, -78 deg C, 30 min, 2.) THF, a) -78 deg C, 1 h, b) from -78 deg C to RT, 4 h
Multi-step reaction with 2 steps 1: N-methylmorpholine / tetrahydrofuran / 1 h / -78 °C 2: 1.) n-BuLi / 1.) THF, -78 deg C, 30 min, 2.) THF, a) -78 deg C, 1 h, b) from -78 deg C to RT, 4 h
Multi-step reaction with 2 steps 1: N-methylmorpholine / tetrahydrofuran / 1 h / -78 °C 2: 1.) n-BuLi, 2.) N-methylmorpholine / 1.) THF, -78 deg C, 2.) THF, a) -78 deg C, 1 h, b) RT, 4 h

  • 42
  • [ 53774-20-2 ]
  • (S)-4-Benzyl-3-((S)-2-methyl-but-3-enoyl)-oxazolidin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Et3N / tetrahydrofuran / 1 h / -78 °C 2: 1.) n-BuLi, 2.) Et3N / 1.) THF, -78 deg C, 2.) THF, a) -78 deg C, 1 h, b) RT, 4 h
Multi-step reaction with 2 steps 1: Et3N / tetrahydrofuran / 1 h / -78 °C 2: 1.) n-BuLi / 1.) THF, -78 deg C, 30 min, 2.) THF, a) -78 deg C, 1 h, b) from -78 deg C to RT, 4 h
Multi-step reaction with 2 steps 1: N-methylmorpholine / tetrahydrofuran / 1 h / -78 °C 2: 1.) n-BuLi / 1.) THF, -78 deg C, 30 min, 2.) THF, a) -78 deg C, 1 h, b) from -78 deg C to RT, 4 h
Multi-step reaction with 2 steps 1: N-methylmorpholine / tetrahydrofuran / 1 h / -78 °C 2: 1.) n-BuLi, 2.) N-methylmorpholine / 1.) THF, -78 deg C, 2.) THF, a) -78 deg C, 1 h, b) RT, 4 h

  • 43
  • [ 53774-20-2 ]
  • [ 184292-93-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Et3N / tetrahydrofuran / 1 h / -78 °C 2: 1.) n-BuLi, 2.) Et3N / 1.) THF, -78 deg C, 2.) THF, a) -78 deg C, 1 h, b) RT, 4 h
Multi-step reaction with 2 steps 1: Et3N / tetrahydrofuran / 1 h / -78 °C 2: 1.) n-BuLi / 1.) THF, -78 deg C, 30 min, 2.) THF, a) -78 deg C, 1 h, b) from -78 deg C to RT, 4 h
Multi-step reaction with 2 steps 1: N-methylmorpholine / tetrahydrofuran / 1 h / -78 °C 2: 1.) n-BuLi, 2.) Et3N / 1.) THF, -78 deg C, 2.) THF, a) -78 deg C, 1 h, b) RT, 4 h
  • 44
  • [ 53774-20-2 ]
  • [ 110080-01-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: oxalyl chloride / 57 h / 0 - 20 °C 2: NH2OH*HCl, KOH / tetrahydrofuran; methanol / 2.25 h / 0 - 20 °C
  • 45
  • [ 53774-20-2 ]
  • [ 110080-02-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: oxalyl chloride / 57 h / 0 - 20 °C 2: NH2OH*HCl, KOH / tetrahydrofuran; methanol / 2.25 h / 0 - 20 °C 3: pyridine / tetrahydrofuran / 0.5 h / 0 °C
  • 46
  • [ 53774-20-2 ]
  • [ 129085-01-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 75 percent / LiAlH4 / diethyl ether / Heating 2: 1) NaH / 1) DME, reflux, overnight, 2) reflux, 24 h 3: 1) AgBF4, 2) aq. Na2CO3 / 1) CH2Cl2, -60 deg C, then rt, overnight, 2) CH2Cl2, 3 h, reflux 4: hydrazine hydrate / ethanol / 2 h / Heating 5: t-BuOK / dimethylsulfoxide / Ambient temperature 6: H2 / Raney nickel / ethanol / 60 h / 2250.2 Torr
  • 47
  • [ 53774-20-2 ]
  • [ 129085-01-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 75 percent / LiAlH4 / diethyl ether / Heating 2: 1) NaH / 1) DME, reflux, overnight, 2) reflux, 24 h 3: 1) AgBF4, 2) aq. Na2CO3 / 1) CH2Cl2, -60 deg C, then rt, overnight, 2) CH2Cl2, 3 h, reflux 4: hydrazine hydrate / ethanol / 2 h / Heating 5: t-BuOK / dimethylsulfoxide / Ambient temperature 6: H2 / Raney nickel / ethanol / 60 h / 2250.2 Torr
  • 48
  • [ 53774-20-2 ]
  • (Z)-2-<2-<2-(p-Methoxyphenoxy)ethyl>-2-methylcyclobutane>propan-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 75 percent / LiAlH4 / diethyl ether / Heating 2: 1) NaH / 1) DME, reflux, overnight, 2) reflux, 24 h 3: 1) ZnCl2, 2) aq. Na2CO3 / 1) CH2Cl2, rt, overnight, 2) CH2Cl2, reflux 4: hydrazine hydrate / ethanol / 2 h / Heating 5: t-BuOK / dimethylsulfoxide / Ambient temperature 6: H2 / Raney nickel / ethanol / 60 h / 2250.2 Torr
  • 49
  • [ 53774-20-2 ]
  • (E)-2-<2-<2-(p-Methoxyphenoxy)ethyl>-2-methylcyclobutane>propan-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 75 percent / LiAlH4 / diethyl ether / Heating 2: 1) NaH / 1) DME, reflux, overnight, 2) reflux, 24 h 3: 1) ZnCl2, 2) aq. Na2CO3 / 1) CH2Cl2, rt, overnight, 2) CH2Cl2, reflux 4: hydrazine hydrate / ethanol / 2 h / Heating 5: t-BuOK / dimethylsulfoxide / Ambient temperature 6: H2 / Raney nickel / ethanol / 60 h / 2250.2 Torr
  • 50
  • [ 53774-20-2 ]
  • [ 82638-92-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 2: Ph3P-Br2-Et3N 3: 79 percent / CCl4 / 120 h / 30 °C
  • 51
  • [ 53774-20-2 ]
  • [ 82638-95-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 2: Ph3P-Br2-Et3N 3: 24 percent / CCl4 / 35 h / Ambient temperature
  • 52
  • [ 53774-20-2 ]
  • [ 82638-93-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 2: Ph3P-Br2-Et3N 3: 45 percent / CCl4 / 35 h / Ambient temperature
  • 53
  • [ 53774-20-2 ]
  • (-)(R)-2-Methyl-1-isopropylamino-butan [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: SOCl2 2: diethyl ether 3: LiAlH4 / diethyl ether 4: H2 / Pd-CaCO3 / methanol / 760 Torr
  • 54
  • [ 7204-29-7 ]
  • [ 53774-20-2 ]
YieldReaction ConditionsOperation in experiment
1 2M3BA=2-Methyl-3-butenoic acid 2M3BA=2-Methyl-3-butenoic acid CrX=Mixture of Crotyl acetate, 3-Acetoxybutene-1, 3-Iodobutene-1, cis- and trans-crotyl iodides 3PA=cis+trans-3-pentenoic acid
  • 55
  • [ 106-99-0 ]
  • [ 542-28-9 ]
  • [ 53774-20-2 ]
YieldReaction ConditionsOperation in experiment
4.1% 1 Example 1 After 1 hour the butadiene (BD) conversion was 78.3%, the yield of cis- and trans-3-pentenoic acid (3PA) was 90.9%, the yield of 2-methyl-3-butenoic acid (2M3BA) was 4.2% and the yield of valerolactone (VL) was 5.0%. After 5 hours the BD conversion was 98.2%, the yield of 3PA was 74%, the yield of 2M3BA was 4.1% and the yield of valerolactone was 15.6%.
  • 56
  • [ 1617-32-9 ]
  • [ 106-99-0 ]
  • [ 542-28-9 ]
  • [ 53774-20-2 ]
YieldReaction ConditionsOperation in experiment
3.2% 2 Example 2 After 1 hour the butadiene conversion was 52.3% and the 3PA yield was 92.1%, the yield of 2M3BA was 3.2% and the yield of VL was 0.9%.
  • 58
  • [ 1271-19-8 ]
  • [ 927-77-5 ]
  • [ 106-99-0 ]
  • [ 53774-20-2 ]
YieldReaction ConditionsOperation in experiment
85% With hydrogenchloride; air; carbon dioxide In diethyl ether Addn. of n-PrMgBr (Et2O) to stirred Et2O suspn. of Cp2TiCl2 and C4H6 (Ar, 0°C) over 5 min, stirring (30 min) at room temp. Bubbling of CO2 through soln. (1 h, room temp.), hydrolysis with aq. HCl, passing of air into react. mixt. for 15 min.; Filtn. gives Cp2TiCl2 in 93% yield recovery. Addn. of aq. NaOH to filtrate, sepn. of org. layer, discarding; extn. of aq. layer with ether, discarding, addn. of concd. HCl, extn. with ether, drying, concn. in vac. Purifn. by trap-to-trap distn.;
  • 59
  • [ 12087-70-6 ]
  • [ 1271-19-8 ]
  • [ 53774-20-2 ]
YieldReaction ConditionsOperation in experiment
1: 85% 2: 82% With hydrogenchloride; air; carbon dioxide In diethyl ether Passing of gaseous CO2 through Et2O soln. of Ti-compd. (Ar) for 1 h, hydrolysis with aq. HCl and then bubbling of air into react. mixt. for 15 min.; Collecting of pptd. crystals of Cp2TiCl2 by filtn., addn. of aq. NaOH, sepn. of org. layer and discarding. Extn. of aq. layer with ether, discarding, addn. of concd. HCl, extn. with ether, drying, concn. in vac. Purifn. by trap-to-trap distn., (1)H NMR.;
  • 60
  • [ 69079-28-3 ]
  • [ 53774-20-2 ]
YieldReaction ConditionsOperation in experiment
91% With sodium hydroxide; dihydrogen peroxide In methanol; water at 20℃; for 0.0833333h;
  • 61
  • [ 53774-20-2 ]
  • C5H7FO [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine; trifluoro-[1,3,5]triazine In dichloromethane at 0℃; for 2h; Inert atmosphere;
  • 62
  • [ 53774-20-2 ]
  • [ 1193511-13-5 ]
  • [ 1193511-19-1 ]
YieldReaction ConditionsOperation in experiment
54% With Hoveyda-Grubbs catalyst second generation In dichloromethane for 72h; Inert atmosphere; Reflux;
  • 63
  • [ 53774-20-2 ]
  • [ 24400-84-8 ]
  • [ 1193511-17-9 ]
YieldReaction ConditionsOperation in experiment
47% With Hoveyda-Grubbs catalyst second generation In dichloromethane for 72h; Inert atmosphere; Reflux;
  • 64
  • [ 124-38-9 ]
  • [ 106-99-0 ]
  • [ 5204-64-8 ]
  • [ 53774-20-2 ]
YieldReaction ConditionsOperation in experiment
3% Stage #1: carbon dioxide; buta-1,3-diene With triethylaluminum In N,N-dimethyl-formamide; toluene at 20℃; for 39h; Stage #2: With hydrogenchloride In water; N,N-dimethyl-formamide; toluene Cooling;
  • 65
  • [ 124-38-9 ]
  • [ 106-99-0 ]
  • [ 5204-64-8 ]
  • [ 53774-20-2 ]
  • [ 13201-46-2 ]
YieldReaction ConditionsOperation in experiment
3% Stage #1: carbon dioxide; buta-1,3-diene With triethylaluminum In tetrahydrofuran; toluene at 20℃; for 40h; Stage #2: With hydrogenchloride In tetrahydrofuran; water; toluene Cooling;
3% Stage #1: carbon dioxide; buta-1,3-diene With triethylaluminum In N,N-dimethyl-formamide; toluene at 20℃; for 72h; Stage #2: With hydrogenchloride In water; N,N-dimethyl-formamide; toluene Cooling;
  • 66
  • [ 53774-20-2 ]
  • [ 20626-49-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: pivaloyl chloride; 4-methyl-morpholine / tetrahydrofuran / 2 h / -78 - 0 °C 1.2: 2.58 h / -78 °C 2.1: lithium hydroxide; dihydrogen peroxide / tetrahydrofuran; water / 0.5 h / 0 °C
Multi-step reaction with 2 steps 1.1: 4-methyl-morpholine; pivaloyl chloride / tetrahydrofuran / -78 - 0 °C 1.2: 2 h / -78 °C 2.1: dihydrogen peroxide; lithium hydroxide / water; tetrahydrofuran / 0.5 h / 0 °C
Multi-step reaction with 2 steps 1.1: 4-methyl-morpholine; pivaloyl chloride / tetrahydrofuran / 2 h / -78 - 0 °C 1.2: 2.5 h / -78 °C 2.1: hydrogenchloride / tetrahydrofuran; water; chloroform / 0 °C / pH 3
Multi-step reaction with 2 steps 1.1: 4-methyl-morpholine; pivaloyl chloride / tetrahydrofuran / -78 - 0 °C 1.2: 1.58 h / -78 °C 2.1: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water / 0.5 h / 0 °C
Multi-step reaction with 2 steps 1.1: 4-methyl-morpholine; pivaloyl chloride / tetrahydrofuran / 2 h / -78 - 0 °C 1.2: 2.58 h / -78 °C 2.1: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water / 0.5 h / 0 °C
Stage #1: 2-methylbut-3-enoic acid With (<i>S</i>)-1-phenyl-ethylamine In acetone at 80℃; for 0.666667h; Stage #2: With hydrogenchloride In water at 20 - 30℃; for 0.666667h; B.2; B.3 Step 2 : Preparation of (R)-2-methylbut-3-enoic acid (S)-1-phenyl-ethane salt (SM-2-4) Compound SM-2-2 (48g, 48mmol) was dissolved in acetone (100 mL) was added Compound SM-2-3 (67mL, 52mmol), refluxed for 40min 80C , natural cooling after crystallization.After suction filtration, the filter cake was added 50mL of acetone, dissolved by heating, crystallization at room temperature, suction-filtered to give the target molecule SM-2-4 (20.5g, 19%, dr≈2/1).Compound SM-2-4 (22g, 99mmol) was dissolved in 1N hydrochloric acid solution (135mL) was stirred at rt 40min, after-treatment to give SM-2 (9.8g, 98%)
Multi-step reaction with 2 steps 1.1: 4-methyl-morpholine; pivaloyl chloride / tetrahydrofuran / 2 h / -78 - 0 °C 1.2: 2 h / -78 °C / Inert atmosphere 2.1: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water / 1.25 h / -1.5 - 1 °C

  • 67
  • [ 53774-20-2 ]
  • [ 1422387-22-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: pivaloyl chloride; 4-methyl-morpholine / tetrahydrofuran / 2 h / -78 - 0 °C 1.2: 2.58 h / -78 °C 2.1: lithium hydroxide; dihydrogen peroxide / tetrahydrofuran; water / 0.5 h / 0 °C 3.1: 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; pyridine / ethyl acetate / -10 - 20 °C / Inert atmosphere 4.1: toluene-4-sulfonic acid / dichloromethane / 1 h / Inert atmosphere; Reflux 4.2: 4 h / Inert atmosphere; Reflux
Multi-step reaction with 4 steps 1.1: 4-methyl-morpholine; pivaloyl chloride / tetrahydrofuran / -78 - 0 °C 1.2: 2 h / -78 °C 2.1: dihydrogen peroxide; lithium hydroxide / water; tetrahydrofuran / 0.5 h / 0 °C 3.1: 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; pyridine / ethyl acetate / -10 - 20 °C 4.1: toluene-4-sulfonic acid / dichloromethane / 1 h / Inert atmosphere; Reflux 4.2: 4 h / Inert atmosphere; Reflux
Multi-step reaction with 4 steps 1.1: 4-methyl-morpholine; pivaloyl chloride / tetrahydrofuran / 2 h / -78 - 0 °C 1.2: 2 h / -78 °C / Inert atmosphere 2.1: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water / 1.25 h / -1.5 - 1 °C 3.1: pyridine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / ethyl acetate / -10 - 20 °C 4.1: toluene-4-sulfonic acid; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 5 h / 40 °C / Inert atmosphere
  • 68
  • [ 53774-20-2 ]
  • [ 1422387-18-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: pivaloyl chloride; 4-methyl-morpholine / tetrahydrofuran / 2 h / -78 - 0 °C 1.2: 2.58 h / -78 °C 2.1: lithium hydroxide; dihydrogen peroxide / tetrahydrofuran; water / 0.5 h / 0 °C 3.1: 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; pyridine / ethyl acetate / -10 - 20 °C / Inert atmosphere 4.1: toluene-4-sulfonic acid / dichloromethane / 1 h / Inert atmosphere; Reflux 4.2: 4 h / Inert atmosphere; Reflux 5.1: palladium 10% on activated carbon; hydrogen / methanol / 20 h / 2585.81 Torr / Inert atmosphere
Multi-step reaction with 5 steps 1.1: 4-methyl-morpholine; pivaloyl chloride / tetrahydrofuran / -78 - 0 °C 1.2: 2 h / -78 °C 2.1: dihydrogen peroxide; lithium hydroxide / water; tetrahydrofuran / 0.5 h / 0 °C 3.1: 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; pyridine / ethyl acetate / -10 - 20 °C 4.1: toluene-4-sulfonic acid / dichloromethane / 1 h / Inert atmosphere; Reflux 4.2: 4 h / Inert atmosphere; Reflux 5.1: hydrogen; palladium 10% on activated carbon / methanol / 20 h / 2585.81 Torr / Inert atmosphere
Multi-step reaction with 5 steps 1.1: 4-methyl-morpholine; pivaloyl chloride / tetrahydrofuran / 2 h / -78 - 0 °C 1.2: 2 h / -78 °C / Inert atmosphere 2.1: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water / 1.25 h / -1.5 - 1 °C 3.1: pyridine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / ethyl acetate / -10 - 20 °C 4.1: toluene-4-sulfonic acid; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 5 h / 40 °C / Inert atmosphere 5.1: hydrogen; palladium 10% on activated carbon / methanol; tetrahydrofuran / 22 h / 20 °C / 2844.39 Torr
  • 69
  • [ 53774-20-2 ]
  • methyl N-[(10R,14S)-14-amino-10-methyl-9-oxo-8,16-diazatricyclo[13.3.1.02,7]-nonadeca-1(19),2(7),3,5,15,17-hexaen-5-yl]carbamate bis-trifluoroacetic acid salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: pivaloyl chloride; 4-methyl-morpholine / tetrahydrofuran / 2 h / -78 - 0 °C 1.2: 2.58 h / -78 °C 2.1: lithium hydroxide; dihydrogen peroxide / tetrahydrofuran; water / 0.5 h / 0 °C 3.1: 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; pyridine / ethyl acetate / -10 - 20 °C / Inert atmosphere 4.1: toluene-4-sulfonic acid / dichloromethane / 1 h / Inert atmosphere; Reflux 4.2: 4 h / Inert atmosphere; Reflux 5.1: palladium 10% on activated carbon; hydrogen / methanol / 20 h / 2585.81 Torr / Inert atmosphere 6.1: dichloromethane / 1 h / 20 °C
Multi-step reaction with 6 steps 1.1: 4-methyl-morpholine; pivaloyl chloride / tetrahydrofuran / -78 - 0 °C 1.2: 2 h / -78 °C 2.1: dihydrogen peroxide; lithium hydroxide / water; tetrahydrofuran / 0.5 h / 0 °C 3.1: 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; pyridine / ethyl acetate / -10 - 20 °C 4.1: toluene-4-sulfonic acid / dichloromethane / 1 h / Inert atmosphere; Reflux 4.2: 4 h / Inert atmosphere; Reflux 5.1: hydrogen; palladium 10% on activated carbon / methanol / 20 h / 2585.81 Torr / Inert atmosphere 6.1: dichloromethane / 1 h / 20 °C
Multi-step reaction with 6 steps 1.1: 4-methyl-morpholine; pivaloyl chloride / tetrahydrofuran / 2 h / -78 - 0 °C 1.2: 2 h / -78 °C / Inert atmosphere 2.1: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water / 1.25 h / -1.5 - 1 °C 3.1: pyridine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / ethyl acetate / -10 - 20 °C 4.1: toluene-4-sulfonic acid; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 5 h / 40 °C / Inert atmosphere 5.1: hydrogen; palladium 10% on activated carbon / methanol; tetrahydrofuran / 22 h / 20 °C / 2844.39 Torr 6.1: dichloromethane / 1 h / 20 °C
  • 70
  • [ 53774-20-2 ]
  • (R)-4-(phenylmethyl)-2-oxazolidinone [ No CAS ]
  • (4R)-4-benzyl-3-[(2R)-2-methylbut-3-enoyl]-1,3-oxazolidin-2-one [ No CAS ]
  • (4R)-4-benzyl-3-[(2S)-2-methylbut-3-enoyl]-1,3-oxazolidin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 55% 2: 38% Stage #1: 2-methylbut-3-enoic acid With 4-methyl-morpholine; pivaloyl chloride In tetrahydrofuran at -78 - 0℃; for 2h; Stage #2: (R)-4-(phenylmethyl)-2-oxazolidinone With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2.58333h; Intermediate 35A. (R)-4-Benzyl-3-((R)-2-methylbut-3-enoyl)oxazolidin-2- one: To the solution of 2-methylbut-3-enoic acid (5.59 g, 55.9 mmol) and N- methylmorpholine (6.14 ml, 55.9 mmol) in THF (62 mL) at 0 °C was added pivaloyl chloride (6.87 ml, 55.9 mmol) dropwise. The reaction mixture was cooled down to -78 °C, and stirred for ~2 h. In a separate flask: To the solution of (R)-4-benzyloxazolidin-2- one (8.25 g, 46.6 mmol) in THF (126 mL) at -78 °C was added N-butyllithium (2.5 M in hexane) (20.49 mL, 51.2 mmol) dropwise. After 35 min, this reaction was transferred via cannula to the first reaction. The reaction mixture was stirred at -78 °C for 2 h, then the cold bath was removed, and the reaction was quenched with saturated NH4C1. The reaction was diluted with water and extracted with EtOAc (3x). The combined organic layers were washed with brine, dried over Na2S04, filtered, and concentrated to give a yellow oil (15 g). Purification by silica gel chromatography afforded the desired product (6.59 g, 55%) as a colorless oil. MS (ESI) m/z: 282.1 (M+Na)+. 1H NMR (500 MHz, CDCls) δ 7.36 - 7.19 (m, 5H), 6.03 - 5.93 (m, 1H), 5.23 - 5.10 (m, 2H), 4.69 - 4.63 (m, 1H), 4.51 - 4.43 (m, 1H), 4.23 - 4.15 (m, 2H), 3.29 (dd, J = 13.5, 3.3 Hz, 1H), 2.79 (dd, J = 13.5, 9.6 Hz, 1H), 1.35 (d, J = 6.9 Hz, 3H) ppm. The other diastereomer (R)-4-benzyl- 3-((S)-2-methylbut-3-enoyl)oxazolidin-2-one (4.6 g, 38%) also obtained as a white solid. MS (ESI) m/z: 260.1 (M+H)+.
1: 55% 2: 38% Stage #1: 2-methylbut-3-enoic acid With 4-methyl-morpholine; pivaloyl chloride In tetrahydrofuran at -78 - 0℃; Stage #2: (R)-4-(phenylmethyl)-2-oxazolidinone With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; [00417] Intermediate 45A. (R)-4-Benzyl-3-((R)-2-methylbut-3-enoyl)oxazolidin-2- one: To the solution of 2-methylbut-3 -enoic acid (5.59 g, 55.9 mmol) and N- methylmorpholine (6.14 ml, 55.9 mmol) in THF (62 mL) at 0 °C was added pivaloyl chloride (6.87 ml, 55.9 mmol) dropwise. The reaction mixture was cooled down to -78 °C, and stirred for ~2 h. In a separate flask: To the solution of (R)-4-benzyloxazolidin-2- one (8.25 g, 46.6 mmol) in THF (126 mL) at -78 °C was added dropwise N-butyllithium (2.5 M in hexane) (20.49 mL, 51.2 mmol). After 35 min, this reaction was transferred via cannula to the first reaction. The reaction mixture was stirred at -78 °C for 2 h, then the cold bath was removed, and the reaction was quenched with saturated NH4CI. The reaction was diluted with water and extracted with EtOAc (3x). The combined organic layers were washed with brine, dried over Na2S04, filtered, and concentrated to give a yellow oil (15 g). Purification by silica gel chromatography afforded the desired product (6.59 g, 55%) as a colorless oil. MS(ESI) m/z: 282.1 (M+Na)+. 1H NMR (500 MHz, CDCI3) δ 7.36 - 7.19 (m, 5H), 6.03 - 5.93 (m, 1H), 5.23 - 5.10 (m, 2H), 4.69 - 4.63 (m, 1H), 4.51 - 4.43 (m, 1H), 4.23 - 4.15 (m, 2H), 3.29 (dd, J = 13.5, 3.3 Hz, 1H), 2.79 (dd, J = 13.5, 9.6 Hz, 1H), 1.35 (d, J = 6.9 Hz, 3H) ppm. The other diastereomer (R)-4-benzyl- 3-((S)-2-methylbut-3-enoyl)oxazolidin-2-one (4.6 g, 38%) also obtained as a white solid. MS(ESI) m/z: 260.1 (M+H)+.
1: 55% 2: 38% Stage #1: 2-methylbut-3-enoic acid With 4-methyl-morpholine; pivaloyl chloride In tetrahydrofuran at -78 - 0℃; for 2h; Stage #2: (R)-4-(phenylmethyl)-2-oxazolidinone With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2.58333h; 2A 2A. Preparation of (R)-4-benzyl-3 -((R)-2-methylbut-3 -enoyl)oxazolidin-2-one To the solution of 2-methylbut-3-enoic acid (5.59 g, 55.9 mmol) and NMM (6.14mL, 55.9 mmol) in THF (62 mL) at 0 °C was added pivaloyl chloride (6.87 mL, 55.9mmol) dropwise. The reaction mixture was cooled down to -78 °C, and stirred for 2 h.In a separate flask: To the solution of (R)-4-benzyloxazolidin-2-one (8.25 g, 46.6 mmol)in THF (126 mL) at -78 °C was added 2.5 M nBuLi in hexane (20.49 mL, 51.2 mmol)dropwise. After 35 mm, this reaction was transferred via cannula to the first reaction. The reaction mixture was stirred at -78 °C for 2 h, then the cold bath was removed, and the reaction was quenched with sat NH4C1. The reaction was diluted with water and extracted with EtOAc (3x). The combined organic layers were washed with brine, driedover Na2SO4, filtered, and concentrated to give a yellow oil (15 g). Purification by silica gel chromatography afforded (R)-4-benzyl-3 -((R)-2-methylbut-3 -enoyl)oxazolidin-2-one (6.59 g, 55%) as a colorless oil. MS(ESI) m/z: 282.1 (M+Na). ‘H NMR (500 MHz, CDC13) ö 7.36 - 7.19 (m, 5H), 6.03 - 5.93 (m, 1H), 5.23 - 5.10 (m, 2H), 4.69 - 4.63 (m, 1H), 4.51 -4.43 (m, 1H), 4.23-4.15 (m, 2H), 3.29 (dd, J 13.5, 3.3 Hz, 1H), 2.79 (dd, J= 13.5, 9.6 Hz, 1H), 1.35 (d, J= 6.9 Hz, 3H) ppm. The other diastereomer (R)-4-benzyl-3-((S)-2-methylbut-3-enoyl)oxazolidin-2-one (4.6 g, 38%) was also obtained as a white solid. MS(ESI) m/z: 260.1 (M+H).
1: 55% 2: 38% Stage #1: 2-methylbut-3-enoic acid With 4-methyl-morpholine; pivaloyl chloride In tetrahydrofuran at -78 - 0℃; for 2h; Stage #2: (R)-4-(phenylmethyl)-2-oxazolidinone With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2.5h; 6A 6A. Preparation of (R)-4-benzyl-3-((R)-2-methylbut-3-enoyl)oxazolidin-2-one To the solution of 2-methylbut-3-enoic acid (5.59 g, 55.9 mmol) and NMM (6.14 ml, 55.9 mmol) in THF (62 mL) at 0 °C was added pivaloyl chloride (6.87 ml, 55.9 mmol) dropwise. The reaction mixture was cooled to -78 °C, and stirred for ~2 h. In a separate flask: To the solution of (R)-4-benzyloxazolidin-2-one (8.25 g, 46.6 mmol) in THF (126 mL) at -78 °C was added 2.5 M nBuLi in hexane (20.49 mL, 51.2 mmol) dropwise. After 35 min, this reaction was transferred via cannula to the first reaction. The reaction mixture was stirred at -78 °C for 2 h, then the cold bath was removed, and the reaction was quenched with sat NH4C1. The reaction was diluted with water and extracted with EtOAc (3x). The combined organic layers were washed with brine, dried over Na2S04, filtered, and concentrated to give a yellow oil (15 g). Purification by silica gel chromatography afforded (R)-4-benzyl-3-((R)-2-methylbut-3-enoyl)oxazolidin-2-one (6.59 g, 55%) as a colorless oil. MS(ESI) m/z: 282.1 (M+Na)+. XH NMR (500 MHz, CDCI3) δ 7.36 - 7.19 (m, 5H), 6.03 - 5.93 (m, 1H), 5.23 - 5.10 (m, 2H), 4.69 - 4.63 (m, 1H), 4.51 - 4.43 (m, 1H), 4.23 - 4.15 (m, 2H), 3.29 (dd, J = 13.5, 3.3 Hz, 1H), 2.79 (dd, J = 13.5, 9.6 Hz, 1H), 1.35 (d, J = 6.9 Hz, 3H) ppm. The other diastereomer (R)-4-benzyl- 3-((S)-2-methylbut-3-enoyl)oxazolidin-2-one (4.6 g, 38%) also was obtained as a white solid. MS(ESI) m/z: 260.1 (M+H)+.
1: 55% 2: 38% Stage #1: 2-methylbut-3-enoic acid With 4-methyl-morpholine; pivaloyl chloride In tetrahydrofuran at -78 - 0℃; Stage #2: (R)-4-(phenylmethyl)-2-oxazolidinone With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1.58333h; 1A 1 A. Preparation of (R)-4-Benzyl-3 -((R)-2-methylbut-3 -enoyl)oxazolidin-2-one To the solution of 2-methylbut-3-enoic acid (5.59 g, 55.9 mmol) and NMM (6.14ml, 55.9 mmol) in THF (62 ml) at 0 °C was added pivaloyl chloride (6.87 ml, 55.9 mmol) dropwise. The reaction mixture was cooled to -78 °C, and stirred for 2 h. In aseparate flask: To a solution of (R)-4-benzyloxazolidin-2-one (8.25 g, 46.6 mmol) in THF (126 ml) at -78 °C was added 2.5 M n-BuLi in hexane (20.49 ml, 51.2 mmol) dropwise. After 35 mm, this reaction was transferred via cannula to the first reaction. The reaction mixture was stirred at -78 °C for 2 h, then the cold bath was removed, and the reaction was quenched with sat NH4C1. The reaction was diluted with water andextracted with EtOAc (3 x). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated to give a yellow oil (15 g). Purification by silica gel chromatography afforded(R)-4-b enzyl-3 -((R)-2-methylbut-3 -enoyl)oxazolidin-2-one (6.59 g, 55%) as a colorless oil. MS (ESI) m/z: 282.1 (M+Na)t ‘HNMR (500 IVIFIz, CDC13) ö 7.36-7.19 (m,5H), 6.03 - 5.93 (m, 1H), 5.23 - 5.10 (m, 2H), 4.69 -4.63 (m, 1H), 4.51 -4.43 (m, 1H),4.23 -4.15 (m, 2H), 3.29 (dd, J 13.5, 3.3 Hz, 1H), 2.79 (dd, J 13.5, 9.6 Hz, 1H),1.35 (d, J 6.9 Hz, 3H) ppm. The other diastereomer(R)-4-b enzyl-3 -((S)-2-methylbut-3 -enoyl)oxazolidin-2-one (4.6 g, 38%) also obtainedas a white solid. MS (ESI) m/z: 260.1 (M+H)+
1: 50% 2: 43% Stage #1: 2-methylbut-3-enoic acid With 4-methyl-morpholine; pivaloyl chloride In tetrahydrofuran at -78 - 0℃; for 2h; Stage #2: (R)-4-(phenylmethyl)-2-oxazolidinone With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere;

  • 71
  • [ 53774-20-2 ]
  • [ 1422387-07-2 ]
  • [ 1422387-08-3 ]
YieldReaction ConditionsOperation in experiment
83% With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In ethyl acetate at -10 - 20℃; Inert atmosphere; 11.11G 11G. tert-Butyl N-[(lS)-l-(2-fluoro-5-{4-[(methoxycarbonyl)amino]-2-(2- methylbut-3-enamido)phenyl}pyridin-3-yl)but-3-en-l-yl]carbamate: To a solution of 2- methylbut-3-enoic acid (0.216 mL, 2.091 mmol) and 1 IF (0.900 g, 2.091 mmol) in EtOAc (59.7 mL) was added DIEA (1.095 mL, 6.27 mmol) and the reaction was allowed to cool to -10 °C under argon. To this mixture was added 1-propanephosphonic acid cyclic anhydride in EtOAc (2.464 mL, 4.18 mmol) and the reaction was allowed to stir for 5 min, and then warmed to 0 °C while stirring under argon. The reaction was then slowly allowed to warm to rt and stirred at rt overnight. After overnight stirring, the reaction mixture was concentrated and purified by silica gel chromatography to give 11G (887 mg, 83%) as a white solid. MS (ESI) m/z: 513.1 (M+H)+.
83% With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In ethyl acetate at -10 - 20℃; Inert atmosphere; 1.1G [00440] 1G. Methyl (4-(5-((lS)-l-((fert-butoxycarbonyl)amino)but-3-en-l-yl)-6- fluoropyridin-3-yl)-3-((2-methylbut-3-enoyl)amino)phenyl)carbamate: To a solution of 2-methylbut-3-enoic acid (0.216 mL, 2.091 mmol) and IF (0.900 g, 2.091 mmol) in EtOAc (59.7 mL) was added DIEA (1.095 mL, 6.27 mmol) and the reaction was allowed to cool to -10 °C under argon. To this mixture was then added T3P (2.464 mL, 4.18 mmol) and the reaction was allowed to stir for 5 min at the same temperature and then allowed to warm to 0 °C followed by to rt slowly while stirring under argon at rt. After overnight stirring, the reaction mixture was concentrated and purified by silica gel chromatography to give 1G (887 mg, 83%) as a white solid. MS(ESI) m/z: 513.1 (M+H)+.
83% With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In ethyl acetate at -10 - 20℃; Inert atmosphere;
  • 72
  • [ 53774-20-2 ]
  • [ 1329171-26-7 ]
  • methyl N-(4-{2-[(1S)-1-[(tert-butoxy)carbonyl]amino}but-3-en-1-yl]pyridin-4-yl}-3-(2-methylbut-3-enamido)phenyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In ethyl acetate at -10 - 0℃; for 7h; 12.12I 121. Methyl N-(4- {2- [( 1 S)- 1 - { [(tert-butoxy)carbonyl] amino } but-3 -en- 1 - yl]pyridin-4-yl}-3-(2-methylbut-3-enamido)phenyl)carbamate: To a cooled solution (-10 °C) of 2-methylbut-3-enoic acid (0.456 mL, 4.41 mmol) and 12H (1.82 g, 4.41 mmol) in EtOAc (126 mL) and DIEA (2.312 mL, 13.24 mmol) was added dropwise a solution of 1- propanephosphonic acid cyclic anhydride in EtOAc (5.20 mL, 8.82 mmol). After 5 min, the reaction was allowed to warm to 0 °C. After 7 h, the reaction was stopped and concentrated. Purification by normal phase chromatography gave 121 (1.57 g, 72%) as a mixture of diastereomers and as a yellow solid. MS (ESI) m/z: 495.1 (M+H)+.
72% With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In ethyl acetate at -10 - 0℃; for 7h; 2.2I [00452] 21. Methyl N-(4-{2-[(lS)-l-[(tert-butoxy)carbonyl]amino}but-3-en-l- yl]pyridin-4-yl}-3-(2-methylbut-3-enamido)phenyl)carbamate (Diastereomers): To a cooled solution (-10 °C) of 2-methylbut-3-enoic acid (0.456 mL, 4.41 mmol) and 2H (1.82 g, 4.41 mmol) in EtOAc (126 mL) and DIEA (2.312 mL, 13.24 mmol) was added dropwise a solution of 1-propanephosphonic acid cyclic anhydride in EtOAc (5.20 mL, 8.82 mmol). After 5 min, the reaction was allowed to warm to 0 °C. After 7 h, the reaction was stopped and concentrated. Purification by normal phase chromatography gave 21 (1.57 g, 72%>) as a mixture of diastereomers and as a yellow solid. MS(ESI) m/z: 495.1 (M+H)+.
  • 73
  • [ 53774-20-2 ]
  • [ 1422387-82-3 ]
  • [ 1422387-83-4 ]
YieldReaction ConditionsOperation in experiment
83% With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In ethyl acetate at -10 - 20℃; for 49h; Inert atmosphere; 27.27J 27J. Methyl N-(4-{2-[(lS)-l-[(tert-butoxy)carbonyl]amino}but-3-en-l-yl]- 6-methoxypyridin-4-yl}-3-(2-methylbut-3-enamido)phenyl)carbamate: DIPEA (3.02 mL, 17.29 mmol) was added to a solution of 2-methylbut-3-enoic acid (0.865 g, 8.64 mmol) and 271 (2.55 g, 5.76 mmol) in EtOAc (57.6 ml) at -10 °C under argon. Next, 1- propanephosphonic acid cyclic anhydride (6.79 ml, 11.53 mmol; 50% solution in EtOAc) was added dropwise and the reaction stirred for 1 h under set conditions and then allowed to come to rt. After 48 hours, the reaction was diluted with EtOAc, washed with saturated NaHC03, brine, dried over Na2S04, filtered, and concentrated. Purification by normal phase chromatography gave the desired product (2.52 g, 83%) as a white solid. MS (ESI) m/z: 525.1 (M+H)+.
83% Stage #1: 2-methylbut-3-enoic acid; methyl N-(3-amino-4-{2-[(1S)-1-[(tert-butoxy)carbonyl]amino}but-3-en-1-yl]-6-methoxypyridin-4-yl}phenyl)carbamate With N-ethyl-N,N-diisopropylamine In ethyl acetate at -10℃; Inert atmosphere; Stage #2: With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In ethyl acetate at -10 - 20℃; for 49h; Inert atmosphere; 5.5J methyl N-(4-{2-[(1S)-1-[(tert-butoxy)carbonyl]amino}but-3-en-1-yl]-6-methoxypyridin-4-yl}-3-(2-methylbut-3-enamido)phenyl)carbamate DIPEA (3.02 mL, 17.29 mmol) was added to a solution of 2-methylbut-3-enoic acid (0.865 g, 8.64 mmol) and 5I (2.55 g, 5.76 mmol) in EtOAc (57.6 ml) at -10 °C under argon. Next, 1-propanephosphonic acid cyclic anhydride (6.79 ml, 11.53 mmol; 50% solution inEtOAc) was added dropwise and the reaction stirred for 1 h under set conditions and then allowed to come to rt. After 48 hours, the reaction was diluted withEtOAc, washed with sat. aq. 5 NaHCO3,brine, dried over Na2SO4, filtered, and concentrated. Purification by normalphase chromatography gave 5J (2.52 g, 83%) as a white solid.
  • 74
  • [ 53774-20-2 ]
  • [ 1329171-26-7 ]
  • [ 1422387-23-2 ]
YieldReaction ConditionsOperation in experiment
81% With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In ethyl acetate at -78 - 20℃; Inert atmosphere; 21.21A [00467] 21A. Methyl (3-(but-3-enoylamino)-4-(2-((lS)-l-((tert- butoxycarbonyl)amino)but-3-en-l-yl)pyridin-4-yl)phenyl)carbamate: To a solution of but-3-enoic acid (0.412 mL, 4.85 mmol) in EtOAc (100 mL) was added DIEA (2.54 mL, 14.55 mmol) and 2G (2 g, 4.85 mmol) and the reaction mixture was allowed to cooled to -78 °C under argon. To this mixture was then added T3P (5.71 mL, 9.70 mmol) and the reaction was allowed to stir for 15 min at the same temperature and the reaction temperature was gradually warmed to rt and stirred at rt for overnight. After stirring for overnight at rt, the reaction mixture was concentrated to yield dark brown oil which was purified using silica gel chromatography to yield the desired product (1.88 g, 81%) as a white solid. MS(ESI) m/z: 481.2 (M+H)+.
  • 75
  • [ 53774-20-2 ]
  • [ 1422388-52-0 ]
  • [ 1422387-37-8 ]
YieldReaction ConditionsOperation in experiment
38% Stage #1: 2-methylbut-3-enoic acid With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at 0℃; for 3h; Inert atmosphere; Stage #2: methyl N-(3-amino-4-(6-((1S)-1-((tert-butoxycarbonyl)amino)but-3-en-1-yl)-2-oxo-1,2-dihydropyridin-4-yl)phenyl)carbamate In N,N-dimethyl-formamide at 20℃; for 72h; 29.29I [00505] 291. Methyl (4-(6-((lS)-l-((tert-butoxycarbonyl)amino)but-3-en-l-yl)-2-oxo- l,2-dihydropyridin-4-yl)-3-((2-methylbut-3-enoyl)amino)phenyl)carbamate: Isobutyl chloro formate (0.956 g, 7.00 mmol) was added to 2-methylbut-3-enoic acid (0.701 g, 7.00 mmol) and 4-methylmorpholine (0.770 mL, 7.00 mmol) in THF (33.3 mL) at 0 °C under a nitrogen atmosphere and stirred for 3 h. The resulting solids were filtered off and the filtrate was used directly for next step. To a round bottom flask containing the mixed anhydride, 29H (0.200 g, 0.467 mmol) and 4-methylmorpholine (0.770 ml, 7.00 mmol) in DMF (6 mL) was added portionwise (1 mL) every ten minutes over 1 h. The reaction mixture was then stirred at rt. After 3 d, the reaction mixture was partitioned between EtOAc and 1.0 NaOH (20 mL). The organic layer was washed with 1.0 N NaOH, H20, 1.0 N HC1 solution, H20, and brine. The organic layer was dried, filtered and concentrated. The crude product was again dissolved in THF (20 mL) and treated with NaOH (10 mL, 10.00 mmol). After stirring for 1 h, the reaction mixture was concentrated and purified using reverse phase HPLC to give the desired product (0.09 g, 38%). MS(ESI) m/z: 511.4 (M+H)+.
  • 76
  • [ 124-38-9 ]
  • [ 75851-67-1 ]
  • [ 53774-20-2 ]
YieldReaction ConditionsOperation in experiment
62% Stage #1: carbon dioxide; 4,4,5,5-tetramethyl-2-(1-methyl-2-propenyl)-1,3,2-dioxaborolane With chloro[1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene]copper(I); potassium <i>tert</i>-butylate In tetrahydrofuran at 70℃; for 16h; Inert atmosphere; Sealed tube; Stage #2: With hydrogenchloride In tetrahydrofuran Inert atmosphere; Sealed tube; regioselective reaction;
  • 77
  • [ 124-38-9 ]
  • [ 69611-02-5 ]
  • [ 53774-20-2 ]
YieldReaction ConditionsOperation in experiment
79% Stage #1: carbon dioxide; (E)-2-(but-2-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane With chloro[1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene]copper(I); potassium <i>tert</i>-butylate In tetrahydrofuran at 70℃; for 16h; Inert atmosphere; Sealed tube; Stage #2: With hydrogenchloride In tetrahydrofuran Inert atmosphere; Sealed tube; regioselective reaction;
  • 78
  • [ 53774-20-2 ]
  • C26H35N5O4 [ No CAS ]
  • C31H41N5O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
259 mg With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In acetonitrile at 20℃; for 16h; Inert atmosphere; 20 To 19a (390 mg, 0.67 mmol) in anhydrous dichloromethane (7 ml.) at 0°C and under an atmosphere of nitrogen, was added trimethylsilyl trifluoromethanesulfonate (182 μΙ_, 1.01 mmol). The reaction mixture was stirred at 0°C for 1 hour before quenching with a saturated aqueous solution of sodium hydrogen carbonate and extracting with ethyl actate (2 x). The organic layers were dried over sodium sulfate, filtered and concentrated in vacuo to afford a white solid. The solid was dissolved in anhydrous acetonitrile (4 mL) and 2-methyl-but-3-enoic acid (81 mg, 0.81 mmol), /V-(3-dimethylaminopropyl)-/V'-ethylcarbodiimide hydrochloride (184 mg, 0.94 mmol) and 1-hydroxybenzotriazole monohydrate (103 mg, 0.67 mmol) were added. The reaction was stirred at RT for 16 h and concentrated in vacuo. The residue was purified by silica gel chromatography using /'so-hexanes/ethyl acetate 1 :1 then 1 :3 to give the title compound (259 mg, 69 %) as a clear viscous oil
  • 79
  • [ 14660-45-8 ]
  • [ 75851-67-1 ]
  • [ 53774-20-2 ]
YieldReaction ConditionsOperation in experiment
62% With chloro[1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene]copper(I) In tetrahydrofuran at 70℃; for 16h; Inert atmosphere; Sealed tube; Carboxylation of Allylboronic Pinacol Esters with PMC; GeneralProcedure (Scheme 1) General procedure: In a glovebox, Cu(IPr)Cl (9 mg, 0.02 mmol, 5 mol%) and PMC(45 mg, 0.39 mmol, 1.1 equiv) were charged to a glass reactiontube. A solution of 1 (0.36 mmol) in THF (1 mL) was added, the tube was sealed, taken out of the glovebox, and heated at 70 °C for16 h. After cooling to r.t., H2O (2 mL) was added and the reaction mixture was acidified with aqueous HCl (1 M), and saturated with sodium chloride. After extraction with Et2O (3 × 3 mL), the organic phase was dried over anhydrous sodium sulfate and concentrated under vacuo. The product was purified by silica gel column chromatography.
  • 80
  • [ 53774-20-2 ]
  • (S)-tert-butyl (1-(4-(4-amino-1-(difluoromethyl)-1H-pyrazol-5-yl)pyridin-2-yl)but-3-en-1-yl)carbamate [ No CAS ]
  • tert-butyl ((1S)-1-(4-(1-(difluoromethyl)-4-(2-methylbut-3-enamido)-1H-pyrazol-5-yl)pyridin-2-yl)but-3-en-1-yl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With pyridine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In water; ethyl acetate at 20℃; for 20.5h; Inert atmosphere; 135A 13 5A. Preparation of tert-butyl ((15)-i -(4-( 1 -(difluoromethyl)-4-(2-methylbut-3 - enamido)- 1 H-pyrazol-5 -yl)pyridin-2-yl)but-3 -en-i -yl)carbamate To a N2 flushed, 3-necked, 250 mL RBF was added a solution of (S)-tert-butyl (1- (4-(4-amino- 1 -(difluoromethyl)- 1H-pyrazol-5 -yl)pyridin-2-yl)but-3 -en-i -yl)carbamate (1.8 g, 4.74 mmol), prepared as described in Intermediate 30C, and EtOAc (20 mL). The solution was cooled to -10 °C and (±)-2-methylbut-3-enoic acid (0.475 g, 4.74 mmol), pyridine (0.767 mL, 9.49 mmol), and T3P (4.24 mL, 7.12 mmol) were added. Thecooling bath was removed and the solution was allowed to warm to rt and then stir over a period of 20 h. Water (15 mL) and EtOAc (15 mL) were added and the mixture was stirred for 30 mm. The organic phase was separated and the aqueous layer was extracted with EtOAc (30 mL). The combined organic extracts were washed with brine (50 mL), dried over Na2SO4, filtered and concentrated. Purification by normal phasechromatography eluting with a gradient of hexanes/EtOAc gave racemic tert-butyl ((iS)1 -(4-( 1 -(difluoromethyl)-4-(2-methylbut-3 -enamido)- 1 H-pyrazol-5 -yl)pyridin-2-yl)but-3 - en-i-yl)carbamate (1.7 g, 3.50 mmol, 74% yield). MS(ESI) m/z: 462.4 [M+H].
  • 81
  • [ 578-66-5 ]
  • [ 53774-20-2 ]
  • 2-methyl-N-(quinolin-8-yl)but-3-enamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% With dmap; N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride In dichloromethane at 20℃; for 16h;
43% With N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 21 - 24℃; for 16h;
With pyridine; O-(7-azabenzotriazol-1-yl)-n,n,n',n'-tetramethyluronium hexafluoro-phosphate In dichloromethane at 20℃; for 16h;
With pyridine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃;
With pyridine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃;
With N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃;
With dmap; N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride In dichloromethane at 20℃;

  • 82
  • [ 53774-20-2 ]
  • ethyl 2-(4-(2-amino-4-nitrophenyl)pyridin-2-yl)pent-4-enoate [ No CAS ]
  • ethyl 2-(4-(2-(2-methylbut-3-enamido)-4-nitrophenyl)pyridin-2-yl)pent-4-enoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In ethyl acetate at 20℃; 15.D STEP D: ethyl 2-(4-(2-(2-methylbut-3 -enamido)-4-nitrophenyl)pyridin-2-yl)pent-4-enoate To a stirred solution of ethyl 2-(4-(2-amino-4-nitrophenyl)pyridin-2-yl)pent-4-enoate (1.6 g, 4.69 mmol) in ethyl acetate (18.03 ml) was added 2-methyl-3-butenoic acid (0.700 ml, 6.09 mmol),T3P (5.58 ml, 9.37 mmol) and DIPEA (2.456 ml, 14.06 mmol) at RT. The reaction mixture was stirred at RT overnight. The reaction mixture was diluted with EtOAc and the organi layer was washed with sat. NaHCO3, dired over MgSO4, filtered and concentrated. The cmde product was purified by flash column chromatography on silica gel (EtOAc/Hex = i/i) to give the title compound. LC/MS = 423.91 [M+i]
  • 83
  • [ 53774-20-2 ]
  • C31H43N5O6 [ No CAS ]
  • C31H41N5O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% Stage #1: C31H43N5O6 With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 0℃; for 1h; Inert atmosphere; Stage #2: 2-methylbut-3-enoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In acetonitrile at 20℃; for 16h; 20 To 19a (390 mg, 0.67 mmol) in anhydrous dichloromethane (7 mL) at 0° C. and under an atmosphere of nitrogen, was added trimethylsilyl trifluoromethanesulfonate (182 μL, 1.01 mmol). The reaction mixture was stirred at 0° C. for 1 hour before quenching with a saturated aqueous solution of sodium hydrogen carbonate and extracting with ethyl actate (2×). The organic layers were dried over sodium sulfate, filtered and concentrated in vacuo to afford a white solid. The solid was dissolved in anhydrous acetonitrile (4 mL) and 2-methyl-but-3-enoic acid (81 mg, 0.81 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (184 mg, 0.94 mmol) and 1-hydroxybenzotriazole monohydrate (103 mg, 0.67 mmol) were added. The reaction was stirred at RT for 16 h and concentrated in vacuo. The residue was purified by silica gel chromatography using iso-hexanes/ethyl acetate 1:1 then 1:3 to give the title compound (259 mg, 69%) as a clear viscous oil.
  • 84
  • [ 53774-20-2 ]
  • [ 20781-20-8 ]
  • N-(2,4-dimethoxybenzyl)-2-methylbut-3-enamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% Stage #1: 2-methylbut-3-enoic acid; 2,4-Dimethoxybenzylamine With N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; for 0.05h; Stage #2: With pyridine In dichloromethane at 20℃; for 12h;
  • 85
  • [ 53774-20-2 ]
  • [ 32231-50-8 ]
  • [ 1730-91-2 ]
  • 86
  • [ 13201-46-2 ]
  • [ 53774-20-2 ]
YieldReaction ConditionsOperation in experiment
96% With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78 - 30℃; for 2h; B.1 Step 1 Preparation of 2-methylbut-3-enoic acid (SM-2-2): At -78 deg.] C solution of diisopropylamine (194mL, 1.38mol) was dissolved in tetrahydrofuran (750mL), was added n-butyllithium (500mL, 2.5M in hexanes, 1.25mol), -78 deg.] C maintaining the reaction 1h, was then added SM-2-1 (50.0g, 499mmol) in tetrahydrofuran (250 mL) was stirred at rt for 2h.After handled SM-2-2 (48g, 96%).
  • 87
  • [ 563-52-0 ]
  • [ 124-38-9 ]
  • [ 5204-64-8 ]
  • [ 53774-20-2 ]
YieldReaction ConditionsOperation in experiment
With tetraethylammonium chloride; magnesium In acetonitrile at 0℃; Electrochemical reaction; Overall yield = 48 percentChromat.; regioselective reaction;
  • 88
  • [ 53774-20-2 ]
  • [ 39657-45-9 ]
  • 1-(2-isoxazolidinyl)-2-methyl-3-buten-1-one [ No CAS ]
  • 89
  • [ 53774-20-2 ]
  • [ 5720-05-8 ]
  • [ 51037-05-9 ]
YieldReaction ConditionsOperation in experiment
12.5 mg With propan-1-ol; bis(1,5-cyclooctadiene)nickel (0); potassium <i>tert</i>-butylate; 4-benzyl-4-methyl-2-(pyridin-2-yl)-4,5-dihydrooxazole at 60℃; for 40h; Sealed tube; regioselective reaction;
  • 90
  • [ 53774-20-2 ]
  • [ 5720-05-8 ]
  • [ 51037-05-9 ]
  • [ 105401-60-3 ]
YieldReaction ConditionsOperation in experiment
25.926 % de With propan-1-ol; bis(1,5-cyclooctadiene)nickel (0); potassium <i>tert</i>-butylate at 60℃; for 40h; Sealed tube; Overall yield = 32 percent; Overall yield = 12.2 mg; regioselective reaction;
  • 91
  • [ 53774-20-2 ]
  • [ 1765-93-1 ]
  • 4-(4-fluorophenyl)-2-methylbutanoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
35% With propan-1-ol; bis(1,5-cyclooctadiene)nickel (0); potassium <i>tert</i>-butylate; 4-benzyl-4-methyl-2-(pyridin-2-yl)-4,5-dihydrooxazole at 60℃; for 40h; Sealed tube; regioselective reaction;
  • 92
  • [ 53774-20-2 ]
  • 2-(5-(p-tolyl)-1H-imidazol-2-yl)piperidine [ No CAS ]
  • 2-methyl-1-(2-(5-(p-tolyl)-1H-imidazol-2-yl)piperidin-1-yl)but-3-en-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% Stage #1: 2-methyl-3-butenoic acid With benzotriazol-1-ol; N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 0.5h; Stage #2: 2-(5-(p-tolyl)-1H-imidazol-2-yl)piperidine With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 16h; 39 Example 39: 2-methyl-1-(2-(5-(p-tolyl)-1H-imidazol-2-yl)piperidin-1-yl)but-3-en-1-one To a solution of 2-methylbut-3-enoic acid (0.597 g, 5.97 mmol) in dichloromethane (100 mL) was added HOBt (0.914 g, 5.97 mmol) and 3-(((ethylimino)methylene)amino)-N,N- dimethylpropan-1-amine (0.926 g, 5.97 mmol) at 0~5 °C and the mixture was stirred at rt. for 0.5 h. Then 2-(5-(p-tolyl)-1H-imidazol-2-yl)piperidine (1.2 g, 4.97 mmol) and DIPEA (1.563 ml, 8.95 mmol) was added and the mixture was stirred at rt. for 16 h. The suspension was filtered and solvent was removed and the crude product was purified by silica gel chromatography (hexane : MTBE = 3 : 1) to give 2-methyl-1-(2-(5-(p-tolyl)- 1H-imidazol-2-yl)piperidin-1-yl)but-3-en-1-one (808 mg, yield: 50 %) as white solid. GC/MS (EI, mixture of stereoisomers, ratio 1:2): isomer 1: m/z (%):323 (2) [M+], 268 (5), 240 (100), 172 (95), 117 (7), 84 (3), 55 (11). isomer 2: m/z (%):323 (2) [M+], 268 (5), 240 (100), 211 (6), 172 (81), 117 (7), 84 (2), 55 (10).1H NMR (300 MHz, DMSO-d6, mixture of stereoisomers and tautomers) δ 12.06, 11.81 (brs, 1H), 7.69 - 7.62 (m, 2H), 7.49 (s, 1H), 7.15 (d, J = 7.3 Hz, 2H), 6.12 - 5.70 (m, 2H), 5.47 - 4.81 (m, 2H), 4.63 - 2.90 (m, 3H), 2.81 - 2.35 (m, 1H), 2.29 (s, 3H), 1.78 - 1.29 (m, 5H), 1.17 (t, J = 5.6 Hz, 3H).13C NMR (75 MHz, DMSO-d6, mixture of stereoisomers and tautomers) δ 172.7 (q), 172.5 (q), 172.3 (q), 147.1 (q), 146.7 (q), 140.3 (q), 139.8 (q), 139.6 (t), 139.1 (t), 135.3 (q), 132.7 (q), 129.4 (t), 124.6 (t), 115.4 (d), 115.3 (d), 113.0 (t), 112.6 (t), 51.7 (t), 51.3 (t), 47.0 (t), 46.8 (t), 42.8 (d), 42.6 (d), 40.2 (t), 39.3 (t), 38.6 (d), 28.4 (d), 28.1 (d), 26.1 (d), 25.8 (d), 25.3 (d), 21.2 (s), 20.3 (d), 20.1 (d), 18.4 (s), 18.2 (s), 18.0 (s) ppm
50% Stage #1: 2-methyl-3-butenoic acid With benzotriazol-1-ol; N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride In dichloromethane at 0 - 5℃; for 0.5h; Stage #2: 2-(5-(p-tolyl)-1H-imidazol-2-yl)piperidine With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 16h; 3.3a Example 3a: 2-methyl-1-(2-(5-(p-tolyl)-1H-imidazol-2-yI)piperidin-1-yl)but-3-en-1-one: To a solution of 2-methylbut-3-enoic acid (0.597 g, 5.97 mmol) in dichloromethane (100 mL) was added HOBt (0.914 g, 5.97 mmol) and 3-(((ethylimino)methylene)amino)-A/,A/- dimethylpropan-1-amine (0.926 g, 5.97 mmol) at 0~5 °C and the mixture was stirred at room temperature for 0.5 h. Then 2-(5-(p-tolyl)-1H-imidazol-2-yl)piperidine (1.2 g, 4.97 mmol) and DIPEA (1 .563 ml, 8.95 mmol) was added and the mixture was stirred at rt. for 16 h. The suspension was filtered and solvent was removed and the crude product was purified by silica gel chromatography (hexane : MTBE = 3 : 1) to give 2-methyl-1- (2-(5-(p-tolyl)-1/7-imidazol-2-yl)piperidin-1-yl)but-3-en-1-one (808 mg, yield: 50 %) as white solid. GC/MS (El, mixture of stereoisomers, ratio 1 :2): isomer 1 : mlz (%):323 (2) [/Vf], 268 (5), 240 (100), 172 (95), 117 (7), 84 (3), 55 (11). isomer 2: mlz (%):323 (2) [/Vf], 268 (5), 240 (100), 211 (6), 172 (81), 117 (7), 84 (2), 55 (10). 1H NMR (300 MHz, DMSO-d6, mixture of stereoisomers and tautomers) 5 12.06, 11 .81 (brs, 1H), 7.69 - 7.62 (m, 2H), 7.49 (s, 1H), 7.15 (d, J = 7.3 Hz, 2H), 6.12 - 5.70 (m, 2H), 5.47 - 4.81 (m, 2H), 4.63 - 2.90 (m, 3H), 2.81- 2.35 (m, 1H), 2.29 (s, 3H), 1 .78 -1 .29 (m, 5H), 1 .17 (t, J = 5.6 Hz, 3H). 13C NMR (75 MHz, DMSO-d6, mixture of stereoisomers and tautomers) 5 172.7 (q), 172.5 (q), 172.3 (q), 147.1 (q), 146.7 (q), 140.3 (q), 139.8 (q), 139.6 (t), 139.1 (t), 135.3 (q), 132.7 (q), 129.4 (t), 124.6 (t), 115.4 (d), 115.3 (d), 113.0 (t), 112.6 (t), 51.7 (t), 51.3 (t), 47.0 (t), 46.8 (t), 42.8 (d), 42.6 (d), 40.2 (t), 39.3 (t), 38.6 (d), 28.4 (d), 28.1 (d), 26.1 (d), 25.8 (d), 25.3 (d), 21.2 (s), 20.3 (d), 20.1 (d), 18.4 (s), 18.2 (s), 18.0 (s) ppm.
  • 93
  • [ 53774-20-2 ]
  • 2,3-dimethyl-3-mercaptopropionic acid [ No CAS ]
  • 4-mercapto-2-methylbutanoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 60% 2: 40% With hydrogen sulfide; C8H20N2O*C2HF6NO4S2 at 120℃; for 6h; 28 The raw material is 2-methyl-3-butenoic acid, the catalyst is [BDMAEEH][Tf2N], the percentage of the catalyst in the raw material is 10 mol%, and H2S is bubbled into the bottom of the reactor. The operating temperature of the reaction unit is 120°C, and the operating pressure is 1 MPa. After 6 hours of reaction, the feed liquid containing the catalyst and the product is pumped into the flash tower, the H2S gas dissolved in the system is vaporized for recycling, and then the remaining mixture is passed into the extraction tower to add water for aqueous liquid-liquid extraction. After liquid-liquid extraction, the ionic liquid in the lower oil phase can be recycled for 1 hour. The upper water phase is the target product aqueous solution, which is passed into the vacuum distillation system unit for vacuum distillation operation, except for the target product as In addition to high-purity and high-value-added products, the water, raw materials and a small amount of ionic liquid obtained from rectification can all be recycled. The target product aqueous solution enters the vacuum distillation system for distillation to obtain 3-mercapto-2-methylpropionic acid and 2-mercapto-2-methylpropionic acid. The temperature of the bottom of the vacuum distillation tower is 100°C, the temperature at the top of the tower is 60°C, the pressure at the bottom of the tower is 10kPa, and the pressure at the top of the tower is 5kPa. Result analysis: The conversion rate of 2-methyl-3-butenoic acid is 90%, the selectivity of 4-mercapto-2-methylbutanoic acid is 60%, and the selectivity of 3-mercapto-2-methylbutanoic acid is 40%.
  • 94
  • [ 563-52-0 ]
  • [ 124-38-9 ]
  • [ 1617-32-9 ]
  • [ 53774-20-2 ]
YieldReaction ConditionsOperation in experiment
With dichloro(bis(diphenylphosphino)methane)nickel(II); tetraethylammonium iodide In N,N-dimethyl-formamide at 0℃; Electrolysis; Overall yield = 44 percentChromat.; regioselective reaction;
  • 95
  • [ 4894-61-5 ]
  • [ 124-38-9 ]
  • [ 1617-32-9 ]
  • [ 53774-20-2 ]
YieldReaction ConditionsOperation in experiment
With dichloro(bis(diphenylphosphino)methane)nickel(II); tetraethylammonium iodide In N,N-dimethyl-formamide at 0℃; Electrolysis; Overall yield = 56 percentChromat.; regioselective reaction;
  • 96
  • [ 53774-20-2 ]
  • [ 62-53-3 ]
  • [ 80188-12-1 ]
YieldReaction ConditionsOperation in experiment
89% With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; for 16h;
Stage #1: 2-methylbut-3-enoic acid With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; for 0.0833333h; Inert atmosphere; Stage #2: aniline In dichloromethane at 0 - 20℃; for 12h; Inert atmosphere;
  • 97
  • [ 625-38-7 ]
  • [ 75-03-6 ]
  • [ 53774-20-2 ]
YieldReaction ConditionsOperation in experiment
Stage #1: but-3-enoic acid With lithium dipropan-2-ylazanide In tetrahydrofuran at 0℃; for 0.75h; Stage #2: ethyl iodide In tetrahydrofuran at 0 - 20℃; for 3.5h; Stage #3: With hydrogenchloride In tetrahydrofuran; water monomer
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