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[ CAS No. 1000-50-6 ] {[proInfo.proName]}

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Chemical Structure| 1000-50-6
Chemical Structure| 1000-50-6
Structure of 1000-50-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1000-50-6 ]

CAS No. :1000-50-6 MDL No. :MFCD00015727
Formula : C6H15ClSi Boiling Point : -
Linear Structure Formula :- InChI Key :MXOSTENCGSDMRE-UHFFFAOYSA-N
M.W :150.72 Pubchem ID :66079
Synonyms :

Calculated chemistry of [ 1000-50-6 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 3
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 43.62
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
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) : -4.61 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.63
Log Po/w (XLOGP3) : 3.67
Log Po/w (WLOGP) : 3.23
Log Po/w (MLOGP) : 2.96
Log Po/w (SILICOS-IT) : 1.04
Consensus Log Po/w : 2.7

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.89
Solubility : 0.195 mg/ml ; 0.00129 mol/l
Class : Soluble
Log S (Ali) : -3.36
Solubility : 0.0659 mg/ml ; 0.000437 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.96
Solubility : 0.166 mg/ml ; 0.0011 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.89

Safety of [ 1000-50-6 ]

Signal Word:Danger Class:8,3
Precautionary Statements:P210-P280-P305+P351+P338-P310 UN#:2986
Hazard Statements:H314-H226-H290 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1000-50-6 ]

* 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 [ 1000-50-6 ]

[ 1000-50-6 ] Synthesis Path-Downstream   1~80

  • 1
  • [ 3121-76-4 ]
  • [ 1000-50-6 ]
YieldReaction ConditionsOperation in experiment
With aluminium trichloride In dichloromethane Ambient temperature;
  • 2
  • [ 554-14-3 ]
  • [ 1000-50-6 ]
  • [ 153880-53-6 ]
YieldReaction ConditionsOperation in experiment
83% With n-butyllithium In diethyl ether; cyclohexane at -20℃; for 1h;
  • 3
  • [ 6262-42-6 ]
  • [ 1000-50-6 ]
  • 1,2,3,1',2',3'-Hexakis-(butyl-dimethyl-silanyl)-bicyclopropyl-2,2'-diene [ No CAS ]
YieldReaction ConditionsOperation in experiment
11% With magnesium In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide at 0℃;
  • 4
  • [ 1000-49-3 ]
  • [ 74-87-3 ]
  • [ 1000-50-6 ]
YieldReaction ConditionsOperation in experiment
With Iodine monochloride In tetrachloromethane at 0℃; for 0.5h;
  • 5
  • [ 1000-50-6 ]
  • [ 30488-11-0 ]
  • C8H21NO4S2Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% In acetonitrile for 6h; Ambient temperature;
  • 6
  • [ 1000-50-6 ]
  • [ 76579-64-1 ]
  • {3-[4-(butyl-dimethyl-silanyl)-phenoxy]-propyl}-dimethyl-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With n-butyllithium In tetrahydrofuran
  • 7
  • [ 1000-50-6 ]
  • [ 238093-19-1 ]
  • {3-[4-(butyl-dimethyl-silanyl)-phenoxy]-propyl}-trimethyl-ammonium; iodide [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% In methanol
  • 8
  • [ 1000-50-6 ]
  • [ 82356-80-7 ]
YieldReaction ConditionsOperation in experiment
84% With ammonia In Petroleum ether at 0℃;
  • 9
  • [ 1000-50-6 ]
  • [ 1074-24-4 ]
  • 2,5-bis(butyldimethylsilyl)-p-xylene [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% Stage #1: 2,5-dibromo-p-xylene With magnesium In tetrahydrofuran for 4h; Heating; Stage #2: butyldimethylsilyl chloride In tetrahydrofuran for 24h; Heating;
  • 10
  • [ 1000-50-6 ]
  • Butyl-fluor-dimethyl-silan [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With potassium fluoride In acetonitrile at 20℃; for 16h;
  • 11
  • [ 2615-15-8 ]
  • [ 1000-50-6 ]
  • [ 194281-47-5 ]
YieldReaction ConditionsOperation in experiment
76% With triethylamine
  • 12
  • [ 1000-50-6 ]
  • [ 356068-09-2 ]
  • [ 356068-11-6 ]
YieldReaction ConditionsOperation in experiment
85% With 1H-imidazole In dichloromethane
  • 13
  • [ 766-96-1 ]
  • [ 1000-50-6 ]
  • 1-(4-bromophenylethynyl)-n-butyldimethylsilane [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% Stage #1: 4-bromo-1-ethynylbenzene With isopropylmagnesium bromide In tetrahydrofuran at 0 - 20℃; Stage #2: butyldimethylsilyl chloride In tetrahydrofuran for 2h; 6 i-propylmagnesiumbromide (0.67 M/THF solution, 3.10 mL, 2.1 mmol) was added dropwise to THF solution (15 mL) of 1-bromo-4-ethynylbenzene (382 mg, 2.0 mmol) at 0° C. After the mixture was stirred for 20 minutes, an ice water bath was removed. After stirring at room temperature for 10 minutes, n-butyldimethylsilyl chloride (0.69 mL, 4.0 mmol) was added to the mixture. After stirring for 2 hours, the reaction was terminated by the addition of saturated ammonium chloride solution (5 mL). The reaction mixture was extracted with ethyl acetate, and it was concentrated and thereafter purified by means of flash column chromatography to obtain (4-bromophenylethynyl)-n-butyldimethylsilane (530 mg, isolated yield: 90%).
Stage #1: 4-bromo-1-ethynylbenzene With isopropylmagnesium bromide In tetrahydrofuran at 0 - 20℃; Stage #2: butyldimethylsilyl chloride In tetrahydrofuran at 20℃; for 2h;
  • 14
  • [ 288-32-4 ]
  • [ 761426-57-7 ]
  • [ 1000-50-6 ]
  • [ 761426-58-8 ]
YieldReaction ConditionsOperation in experiment
96% In N,N-dimethyl-formamide A.4 [1 -(4-Fluoro-phenyl)-1H-imidazol-4-yl]-methanol Step 4 4-(tert-Butyl-dimethyl-silanyloxymethyl)-1-(4-fluoro-phenyl)-1H-imidazole [1-(4-Fluoro-phenyl)-1H-imidazol-4-yl]-methanol (13 g, 67.5 mmol) was dissolved 65 mL DMF. Imidazole (11 g, 162 mmol) and tert. butyldimethyl chlorosilane (12.2 g, 81 mmol) were added. The reaction mixture was stirred at 45° C. overnight and poured into 500 mL water. The aqueous phase was extracted three times with ethyl acetate (200 mL each). The combined organic extracts were dried with magnesium sulfate, filtered and evaporated. The crude product was purified by column chromatography on silica gel (methylene chloride/methanol 98:2) and the desired compound was obtained as a light brown oil (20 g, 96%), MS: m/e=291.2 (M-CH3), m/e=249.1 (M-tert. butyl).
  • 15
  • [ 1000-50-6 ]
  • [ 247262-63-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: Mg / tetrahydrofuran / 4 h / Heating 1.2: 53 percent / tetrahydrofuran / 24 h / Heating 2.1: 41 percent / NBS / benzyl peroxide / benzene / 2 h / 20 °C / Irradiation
  • 16
  • [ 1000-50-6 ]
  • [ 153880-48-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 83 percent / BuLi / cyclohexane; diethyl ether / 1 h / -20 °C 2: 82 percent / m-chloroperbenzoic acid / CH2Cl2 / 1 h
  • 17
  • [ 1000-50-6 ]
  • 1-dimethylbutylsilyl-5-(1-piperidino)-(1E,3E)-1,3-pentadiene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 83 percent / BuLi / cyclohexane; diethyl ether / 1 h / -20 °C 2: 82 percent / m-chloroperbenzoic acid / CH2Cl2 / 1 h 3: 50 percent / toluene / 3 h / Heating
  • 18
  • [ 1000-50-6 ]
  • [ 107149-34-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1.) n-BuLi / 1.) THF, RT, 2 h, 2.) THF, RT, 18 h 2: 4percent HCl / methanol / 18 h / Ambient temperature
  • 19
  • [ 1000-50-6 ]
  • (+/-)-4,5-trans-4-(t-butyldimethylsilyloxy)-5-iodomethyl-3-pentylidenetetrahydrofuran-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 2: 70 percent / I2, Na2S2O3 / tetrahydrofuran; H2O / 20 h
  • 20
  • [ 288-32-4 ]
  • [ 1000-50-6 ]
  • [ 82380-18-5 ]
  • 2-fluoro-4-dimethylbutylsilyloxy benzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
In <i>N</i>-methyl-acetamide 2 3-fluoro-4-cyanoethynyl-1-(4-propylphenyl) carbonyloxybenzene (Compound No. 153) EXAMPLE 2 3-fluoro-4-cyanoethynyl-1-(4-propylphenyl) carbonyloxybenzene (Compound No. 153) To a solution of 100 ml of 3-fluoro-4-cyanophenol in 200 ml of dimethylformamide were added 110 mmol of dimethylbutylsilyl chloride and 110 mmol of imidazole while cooling with an ice bath and stirring, the solution was elevated to room temperature and stirred for 3 hours. The solution was placed into water and extracted with toluene. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to afford a colourless oily product. Distillation of the product under reduced pressure gave 100 mmol of 2-fluoro-4-dimethylbutylsilyloxy benzonitrile.
  • 21
  • 2-n-butyl-1-(2-chlorophenyl)methyl-4,5 bis(hydroxy)methyl-1H-imidazole [ No CAS ]
  • [ 1000-50-6 ]
  • [ 133486-39-2 ]
YieldReaction ConditionsOperation in experiment
With dmap; manganese dioxide; triethylamine In dichloromethane 45.i (i) (i) 2-n-butyl-1-(2-chlorophenyl)methyl-4-(t butyldimethylsilyloxy)methyl-1H-imidazol-5-carboxaldehyde A solution of 2-n-butyl-1-(2-chlorophenyl)methyl-4,5 bis(hydroxy)methyl-1H-imidazole (Example 11, (i)(b) (310 mg, 1 mmol) in methylene chloride (5 mL) was treated with 4-dimethylaminopyridine (5.2 mg), triethylamine (1.5 mmol) and t butyl dimethylsilyl chloride (192 mg, 1.24 mmol). The mixture was stirred at 25° C. for 20 hours, diluted with water and the organic layer was washed well with water, dried, concentrated and chromatographed over silica gel with an ethyl acetate/methanol gradient to afford 127 mg (24%) of the bis (4,5 t butyldimethylsilyl) ether and 252 mg (59%) of 2-n butyl-1-(2-chlorophenyl)methyl-4-t-butyldimethysilyloxymethyl-5-hydroxymethyl-1H-imidazole. This monoether (252 mg) was oxidized to the 5-carboxaldehyde using manganese dioxide to provide 170 mg of 2-n-butyl-1-(2-chlorophenyl)methyl-4-(t-butyldimethylsilyloxy)methyl-1H-imidazol-5-carboxaldehyde as an oil.
  • 22
  • [ 288-32-4 ]
  • [ 1000-50-6 ]
  • [ 33697-81-3 ]
  • [ 178486-14-1 ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide 5 Preparation of (3-chloro-4-t.butyldimethylsilyloxy)phenylacetic acid t.butyldimethylsilylester (Intermediate 16) EXAMPLE 5 Preparation of (3-chloro-4-t.butyldimethylsilyloxy)phenylacetic acid t.butyldimethylsilylester (Intermediate 16) Imidazole (1.8 g; 26.4 mmoles) was added, under nitrogen at room temperature, to a solution of (3-chloro-4-hydroxy)phenylacetic acid (1 g; 5.3 mmoles) (Aldrich) and t.butyldimethylsilylchloride (2 g; 13.3 mmoles) in DMF (6 ml). The reaction mixture was kept under stirring at room temperature for 5 hours, then poured into a 5% Na2 CO3 aqueous solution (25 ml) and extracted with hexane (2*30 ml). The organic phase was dried on Na2 SO4 and the solvent was evaporated under reduced pressure obtaining Intermediate 16 (2.2 g) as an oil. 1 H-NMR (200 MHz; CDCl3): δ(ppm): 0.19 (s, 6H); 0.21 (s, 6H); 0.85 (s, 9H); 1.00 (s, 9H); 3.50 (s, 2H); 6.81 (d, 1H); 6.99 (dd, 1H); 7.24 (d, 1H). Mass: 415 [M+1].
In N,N-dimethyl-formamide 5 Preparation of (3-chloro-4-t.butyldimethylsilyloxy)phenylacetic acid t.butyldimethylsilylester (Intermediate 16) Example 5 Preparation of (3-chloro-4-t.butyldimethylsilyloxy)phenylacetic acid t.butyldimethylsilylester (Intermediate 16) Imidazole (1.8 g; 26.4 mmoles) was added, under nitrogen at room temperature, to a solution of (3-chloro-4-hydroxy)phenylacetic acid (1 g; 5.3 mmoles) (Aldrich) and t.butyldimethylsilylchloride (2 g; 13.3 mmoles) in DMF (6 ml). The reaction mixture was kept under stirring at room temperature for 5 hours, then poured into a 5% Na2CO3 aqueous solution (25 ml) and extracted with hexane (2x30 ml). The organic phase was dried on Na2SO4 and the solvent was evaporated under reduced pressure obtaining Intermediate 16 (2.2 g) as an oil. 1H-NMR (200 MHz; CDCl3): δ (ppm): 0.19 (s, 6H); 0.21 (s, 6H); 0.85 (s, 9H); 1.00 (s, 9H); 3.50 (s, 2H); 6.81 (d, 1H); 6.99 (dd, 1H); 7.24 (d, 1H). Mass: 415 [M+1].
  • 23
  • [ 288-32-4 ]
  • [ 1000-50-6 ]
  • [ 115-19-5 ]
  • [ 98733-45-0 ]
YieldReaction ConditionsOperation in experiment
31.81 g (54%) With 2-(Dimethylamino)pyridine In water; N,N-dimethyl-formamide 1 3-Methyl-3-t.butyldimethylsilyloxy-butyne EXAMPLE 1 3-Methyl-3-t.butyldimethylsilyloxy-butyne To the solution of 25 g (0.29 mole) of 3-methyl-3-hydroxy-butyne in 50 ml anhydrous N,N-dimethylformamide was added 44.5 g (0.65 mole) imidazole. After the reaction mixture was cooled in ice bath 50 g (0.33 mole) of t.butyldimethylsilyl chloride was added. The reaction mixture was stirred in ice-bath for 15 minutes and at RT overnight. 250 mg of dimethylaminopyridine was then added and heated for two hours at 70° C. The reaction mixture was poured in 1 liter of cold water and extracted with 5*150 ml of ether. The ether extract was washed with water and brine, dried over magnesium sulfate and evaporated to dryness. Purification was performed by FLASH chromatography on silica-gel column with pentane, and distillation under house vacuum (b.p. 120° C.) to give 31.81 g (54%) of the title compound. 1 H-NMR (CDCl3):δ0.87 (s, 9H), 1.47 (s, 6H), 2.39 (s, 1H). Analysis: Calcd for C11 H22 OSi: C 66.60, H 11.18; Found: C. 66.13, H 11.46.
31.81 g (54%) With 2-(Dimethylamino)pyridine In water; N,N-dimethyl-formamide 1 3-Methyl-3-t.butyldimethylsilyloxy-butyne (formula IX) EXAMPLE 1 3-Methyl-3-t.butyldimethylsilyloxy-butyne (formula IX) To the solution of 25 g (0.29 mole) of 3-methyl-3-hydroxy-butyne in 50 ml anhydrous N,N-dimethylformamide was added 44.5 g (0.65 mole) imidazole. After the reaction mixture was cooled in ice bath 50 g (0.33 mole) of t.butyldimethylsilyl chloride was added. The reaction mixture was stirred in ice-bath for 15 minutes and at RT overnight. 250 mg of dimethylaminopyridine was then added and heated for two hours at 70°C. The reaction mixture was poured in 1 liter of cold water and extracted with 5 x 150 ml of ether. The ether extract was washed with water and brine, dried over magnesium sulfate and evaporated to dryness. Purification was performed by FLASH chromatography on silica-gel column with pentane, and distillation under house vacuum (b.p. 120°C) to give 31.81 g (54%) of the title compound. 1H-NMR (CDCl3): δ 0.87 (s, 9H), 1.47 (s, 6H), 2.39 (s, 1H). Analysis: Calcd for C11H22OSi: C 66.60, H 11.18; Found: C66.13, H 11.46.
  • 24
  • [ 288-32-4 ]
  • [ 1000-50-6 ]
  • [ 60966-36-1 ]
  • 20-α-(t-Butyldimethylsilyloxymethyl)-pregn-4-ene-3-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
1.1 g (70%) In N,N-dimethyl-formamide 1.ii (ii) (ii) 20-α-(t-Butyldimethylsilyloxymethyl)pregn-4-ene-3-one A solution of 20-α-(hydroxymethyl)pregn-4-ene-3-one (1.2 g, 3.5 mmol), t butyldimethylsilyl chloride (627 mg, 4.15 mmol) and imidazole (287 mg, 4.22 mmol) in DMF (40 ml) was stirred overnight at 40° C. The reaction mixture was then poured into ice water and the emulsion was washed three times with ethyl acetate. The organic layers were combined, washed with cold dilute hydrochloric acid, water and brine; dried over sodium sulfate and evaporated to dryness. Recrystallization from methanol afforded 1.1 g (70%) of 20-α-(t-butyldimethylsilyloxymethyl)pregn-4-ene-3-one.
  • 25
  • [ 288-32-4 ]
  • [ 1000-50-6 ]
  • [ 41138-61-8 ]
  • [ 161978-56-9 ]
YieldReaction ConditionsOperation in experiment
In <i>N</i>-methyl-acetamide; Petroleum ether VI.A (R)4-TERT-BUTYLDIMETHYLSILYLOXY-2-(6-CARBOMETHOXYHEXYL)-CYCLOPENT-2-ENONE (5) Step A (R)4-TERT-BUTYLDIMETHYLSILYLOXY-2-(6-CARBOMETHOXYHEXYL)-CYCLOPENT-2-ENONE (5) A solution of (R)4-hydroxy-2-(6-carbomethoxyhexyl)-cyclopent-2-enone (1.34 g; 5.58 mmol), t. butyl dimethylsilyl chloride (1.69 g; 11.2 mmol) and imidazole (0.8 g, 11.7 mmol) in dimethylformamide (11.2 ml) is stirred under nitrogen atmosphere for 30 minutes. The reaction mixture is diluted with petroleum ether, and the organic layer is washed with lN HCl, water, saturated aqueous NaHCO3 and brine. The solvent is evaporated in vacuo. Column chromatographic purification on silica gel, eluding with 5% EtOAc in petroleum ether, gives 1.88 g (95%) or (R)4-t.-butyldimethylsilyloxy-2-(5-carbomethoxyhexyl)-cyclopent-2-enone.
  • 26
  • [ 288-32-4 ]
  • [ 1000-50-6 ]
  • [ 41138-61-8 ]
  • [ 41138-69-6 ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide; Petroleum ether IV.B (3R)3-t.BUTYLDIMETHYLSILYLOXY-5-OXO-1-CYCLOPENTENEHEPTANOIC-ACID, METHYL ESTER (5) Step B (3R)3-t.BUTYLDIMETHYLSILYLOXY-5-OXO-1-CYCLOPENTENEHEPTANOIC-ACID, METHYL ESTER (5) A solution of (3R)3-hydroxy-5-oxo-l-cyclopenteneheptanoic acid, methyl ester (1.34 g, 5.6 mmol), t.butyl dimethylsilyl chloride (1.69 g, 11.2 mmol), and imidazole (0.8 g, 11.2 mmol) in DMF (11.2 ml) is stirred at room temperature for 30 min under N2 atmosphere. Petroleum ether (100 ml) is added, and the organic layer washed with H2), 1 N HCl, brine, concentrated aqueous NaHCO3, and again with brine (each 10 ml). After drying (MgSO4) the solvents are removed on the rotary evaporator (20 Torr, 30° C.) to afford quantitatively (3R)3-t.butyldimethylsilyloxy-5-oxo-l-cyclopenteneheptanoic acid, methyl ester.
  • 27
  • [ 89193-66-8 ]
  • [ 1000-50-6 ]
  • 2-methyl-3-(4-n-butyldimethylsilylphenyl)-propyl chloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
With n-butyllithium In tetrahydrofuran; pentane RECIPE 1 RECIPE 1 10.0 parts of 2-methyl-3-(4-bromophenyl)-propyl chloride were introduced into 80 parts of THF, and a solution of 2.55 parts of n-butyl-lithium in pentane was then added dropwise at from -75° to -70° C. The mixture was then stirred at -50° C. for 30 minutes and 6.6 parts of n-butyldimethylchlorosilane were added dropwise at this temperature. The reaction mixture was subsequently stirred at -50° C. for 30 minutes and then allowed to warm to room temperature, and stirring was continued for 12 hours. The mixture was filtered, the solvent was distilled off and the residue was distilled to give, at a boiling point of 96°-100° C./0.08 mbar, 9.8 parts of 2-methyl-3-(4-n-butyldimethylsilylphenyl)-propyl chloride of nD22 1.5033.
  • 28
  • [ 1000-50-6 ]
  • [ 70384-51-9 ]
  • tetramethyldibutyldisilane [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With sodium iodide; Example 4 The procedure was the same as in Example 1, but 3.5 g of a 9 moles:1 mole mixture of tris(3,6-dioxaheptyl)-amine:NaI were introduced. 33 g of butyldimethylchlorosilane were then introduced in the course of 2 hours. After 8 hours of reaction, tetramethyldibutyldisilane was obtained with a yield of 85percent relative to both the butyldimethylchlorosilane product charged and the butylmethylchlorosilane product converted.
  • 29
  • [ 1000-50-6 ]
  • [ 162976-69-4 ]
  • methyl N-dimethyl-n-butylsilyl-benzimidazole-2-carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With n-butyllithium In tetrahydrofuran; hexane 5 EXAMPLE 5 EXAMPLE 5 3.5 parts of n-butyl-lithium in hexane are added, in portions, to a suspension of 10 parts of methyl benzimidazole-2-carbamate in 100 parts of absolute tetrahydrofuran, under nitrogen at -78° C. The mixture is warmed to room temperature and stirred for 6 hours, after which 9.5 parts of n-butyl-dimethylchlorosilane are added in portions. After stirring for 12 hours, insoluble matter is filtered off and the solvent is removed from the filtrate under reduced pressure. 9.0 parts of methyl N-dimethyl-n-butylsilyl-benzimidazole-2-carbamate remain in the residue; decomposition point >110° C. (active ingredient No. 2). NMR (δ in ppm): 0.5-1.8 (n-C4 H9 (CH3)2 Si, 15H); 3.60 (OCH3, 3H); 6.7-7.6 (aromatic, 4H).
  • 30
  • [ 288-32-4 ]
  • silyl ether (2R,3R)1-benzyloxy-2-t.butyl dimethylsilyloxy-3-methoxy-3-methyl-6-heptene [ No CAS ]
  • [ 1000-50-6 ]
  • [ 122804-37-9 ]
  • [ 122804-38-0 ]
YieldReaction ConditionsOperation in experiment
In Difluoromethane; water 6.F (2R,3R)1-Benzyloxy-2-t.butyl dimethylsilyloxy-3-methoxy-3-methyl-6-heptene Step F (2R,3R)1-Benzyloxy-2-t.butyl dimethylsilyloxy-3-methoxy-3-methyl-6-heptene To a solution of (2R,3R)1-benzyloxy-3-methoxy-3-methyl-6-heptene-2-ol (51.37 g, 194.3 mmol) in anhydrous difluoromethane (500 ml) at room temperature under nitrogen, is added imidazole (2 eq, 26.44 g, 388.5 mmol) followed by t.butyl dimethylsilyl chloride (1.5 eq, 44 g, 291.5 mmol). The mixture is stirred for 2 days. Dichloromethane is removed under reduced pressure, water (1 L) is added, and the mixture is extracted with ethyl ether (2 x 500 ml). The combined organic fraction is washed with 1 N HCl, then saturated NaHCO3 and brine. After drying over sodium sulfate, the solution is evaporated. The residue is filtered through a short path of silica gel, first eluding with petroleum ether to remove the siloxanes, then with petroleum ether/ethyl acetate: 90/10 to collect the silyl ether (2R,3R)1-benzyloxy-2-t.butyl dimethylsilyloxy-3-methoxy-3-methyl-6-heptene (60.6 g, 82.3 %).
  • 31
  • [ 1000-50-6 ]
  • [ 23667-13-2 ]
YieldReaction ConditionsOperation in experiment
81% With water; triethylamine In diethyl ether at 20℃; for 1h;
  • 32
  • [ 1000-50-6 ]
  • [ 21120-36-5 ]
  • [ 1221794-72-4 ]
YieldReaction ConditionsOperation in experiment
70% Stage #1: 1-fluoroethyl phenyl ketone With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; Stage #2: butyldimethylsilyl chloride In tetrahydrofuran at -78 - 20℃; optical yield given as %de;
  • 33
  • [ 930-68-7 ]
  • [ 1974-04-5 ]
  • [ 1000-50-6 ]
  • [ 1286212-48-3 ]
YieldReaction ConditionsOperation in experiment
58 %Chromat. With manganese; (1,2-dimethoxyethane)dichloronickel(II); 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine In N,N-dimethyl-formamide at 40℃; for 24h; Inert atmosphere;
  • 34
  • [ 1000-50-6 ]
  • [ 1403470-77-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 3,4,7,8-Tetramethyl-o-phenanthrolin / cyclohexane / 0.05 h / 80 °C / Inert atmosphere 1.2: 12 h / 80 °C / Inert atmosphere 2.1: triethylamine / cyclohexane / 0.5 h / 20 °C
  • 35
  • [ 1000-50-6 ]
  • [ 1403470-78-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 3,4,7,8-Tetramethyl-o-phenanthrolin / cyclohexane / 0.05 h / 80 °C / Inert atmosphere 1.2: 12 h / 80 °C / Inert atmosphere 2.1: triethylamine / cyclohexane / 0.5 h / 20 °C
  • 36
  • [ 1000-50-6 ]
  • [ 1403470-82-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 3,4,7,8-Tetramethyl-o-phenanthrolin / cyclohexane / 0.05 h / 80 °C / Inert atmosphere 1.2: 12 h / 80 °C / Inert atmosphere 2.1: triethylamine / cyclohexane / 0.5 h / 20 °C
  • 37
  • [ 1000-50-6 ]
  • [ 1403470-83-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 3,4,7,8-Tetramethyl-o-phenanthrolin / cyclohexane / 0.05 h / 80 °C / Inert atmosphere 1.2: 12 h / 80 °C / Inert atmosphere 2.1: triethylamine / cyclohexane / 2 h / 60 °C
  • 38
  • [ 1000-50-6 ]
  • [ 1403470-84-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 3,4,7,8-Tetramethyl-o-phenanthrolin / cyclohexane / 0.05 h / 80 °C / Inert atmosphere 1.2: 12 h / 80 °C / Inert atmosphere 2.1: triethylamine; water / cyclohexane / 0.5 h / 20 °C
  • 39
  • [ 1000-50-6 ]
  • [ 1403470-86-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 3,4,7,8-Tetramethyl-o-phenanthrolin / cyclohexane / 0.05 h / 80 °C / Inert atmosphere 1.2: 12 h / 80 °C / Inert atmosphere 2.1: triethylamine; zinc trifluoromethanesulfonate / toluene / 0.5 h / 20 °C 2.2: 1 h / 20 °C
  • 40
  • [ 1000-50-6 ]
  • [ 1403470-87-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 3,4,7,8-Tetramethyl-o-phenanthrolin / cyclohexane / 0.05 h / 80 °C / Inert atmosphere 1.2: 12 h / 80 °C / Inert atmosphere 2.1: triethylamine / cyclohexane / 0.5 h / 20 °C 3.1: n-butyllithium / tetrahydrofuran / 6 h / -78 - 20 °C / Inert atmosphere
  • 41
  • [ 1000-50-6 ]
  • [ 1403470-88-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 3,4,7,8-Tetramethyl-o-phenanthrolin / cyclohexane / 0.05 h / 80 °C / Inert atmosphere 1.2: 12 h / 80 °C / Inert atmosphere 2.1: triethylamine / cyclohexane / 0.5 h / 20 °C 3.1: 1,1'-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex; cesiumhydroxide monohydrate / 1,4-dioxane / 24 h / 80 °C / Inert atmosphere
  • 42
  • [ 1000-50-6 ]
  • [ 73183-34-3 ]
  • [ 1403470-76-7 ]
YieldReaction ConditionsOperation in experiment
84% With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 3,4,7,8-tetramethylphenanthroline In cyclohexene at 80℃; for 12h;
Stage #1: bis(pinacol)diborane With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 3,4,7,8-Tetramethyl-o-phenanthrolin In cyclohexane at 80℃; for 0.05h; Inert atmosphere; Stage #2: butyldimethylsilyl chloride In cyclohexane at 80℃; for 12h; Inert atmosphere;
  • 43
  • [ 1000-50-6 ]
  • [ 95-56-7 ]
  • C12H19BrOSi [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-hydroxybromobenzene With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 1h; Inert atmosphere; Stage #2: butyldimethylsilyl chloride In tetrahydrofuran; mineral oil at 0 - 20℃; Inert atmosphere;
  • 44
  • [ 930-68-7 ]
  • [ 591-50-4 ]
  • [ 1000-50-6 ]
  • [ 1416985-43-7 ]
YieldReaction ConditionsOperation in experiment
79% With bis(acetylacetonate)nickel(II); manganese; 2.9-dimethyl-1,10-phenanthroline In N,N-dimethyl acetamide at 20℃;
  • 45
  • [ 1000-50-6 ]
  • [ 94427-72-2 ]
  • tert-butyldimethyl(nona-1,8-dien-5-yloxy)silane [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% Stage #1: 1,8-nonadiene-5-ol With 1H-imidazole In dichloromethane at 20℃; for 0.25h; Stage #2: butyldimethylsilyl chloride In dichloromethane at 0℃; tert-Butyldimethylsiloxydienes 7a, 8a, and 9a General procedure: To a solution of dienol (1 equiv) in CH2Cl2 (20 mL), imidazole (2 equiv) was added at r.t., and mixture was stirred for 15 min. To the stirred solution, a solution of TBSCl (1.5 equiv) in CH2Cl2 (5 mL), was added slowly at 0 °C and stirring was continued overnight. The mixture was poured into H2O (50 mL) and extracted with CH2Cl2 (3× 50 mL). The combined organic layers were dried (anhydrous Na2SO4), and concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel) to afford the desired TBS ether.
  • 46
  • [ 1000-50-6 ]
  • [ 58728-81-7 ]
  • 4-(tert-butyldimethylsiloxy)octa-1,7-diene [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% Stage #1: octa-1,7-dien-4-ol With 1H-imidazole In dichloromethane at 20℃; for 0.25h; Stage #2: butyldimethylsilyl chloride In dichloromethane at 0℃; tert-Butyldimethylsiloxydienes 7a, 8a, and 9a General procedure: To a solution of dienol (1 equiv) in CH2Cl2 (20 mL), imidazole (2 equiv) was added at r.t., and mixture was stirred for 15 min. To the stirred solution, a solution of TBSCl (1.5 equiv) in CH2Cl2 (5 mL), was added slowly at 0 °C and stirring was continued overnight. The mixture was poured into H2O (50 mL) and extracted with CH2Cl2 (3× 50 mL). The combined organic layers were dried (anhydrous Na2SO4), and concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel) to afford the desired TBS ether.
  • 47
  • [ 1000-50-6 ]
  • [ 2883-45-6 ]
  • [ 139656-31-8 ]
YieldReaction ConditionsOperation in experiment
98% Stage #1: 1, 6-heptadien-4-ol With 1H-imidazole In dichloromethane at 20℃; for 0.25h; Stage #2: butyldimethylsilyl chloride In dichloromethane at 0℃; tert-Butyldimethylsiloxydienes 7a, 8a, and 9a General procedure: To a solution of dienol (1 equiv) in CH2Cl2 (20 mL), imidazole (2 equiv) was added at r.t., and mixture was stirred for 15 min. To the stirred solution, a solution of TBSCl (1.5 equiv) in CH2Cl2 (5 mL), was added slowly at 0 °C and stirring was continued overnight. The mixture was poured into H2O (50 mL) and extracted with CH2Cl2 (3× 50 mL). The combined organic layers were dried (anhydrous Na2SO4), and concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel) to afford the desired TBS ether.
  • 48
  • [ 1000-50-6 ]
  • [ 38274-16-7 ]
  • C17H28Si2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-bromo-1-(trimethylsilylethynyl)benzene With n-butyllithium In tetrahydrofuran at -78℃; for 0.166667h; Stage #2: butyldimethylsilyl chloride In tetrahydrofuran at -78 - 20℃; for 1h;
  • 49
  • [ 1000-50-6 ]
  • [ 1817-57-8 ]
  • 1-butyldimethylsilyl-3-butyldimethylsilyloxy-1-phenylbuta-1,2-diene [ No CAS ]
YieldReaction ConditionsOperation in experiment
41 %Spectr. With magnesium In N,N-dimethyl-formamide at 25℃; for 5h; Inert atmosphere; General procedure for reductive coupling reaction between ynone 1,3 or 5 and chlorotrialkylsilane General procedure: A typical procedure is as follows. To magnesium turnings (0.73 g, 30 mmol) for Grignard reagent with no pre-treatment and chlorotrialkylsilane (40 mmol) in dry N,N-dimethylformamide (DMF) (20 mL) in 100mL-four-necked flask, ynone 1 (5 mmol) in DMF (10 mL) was added at25°C dropwise slowly and the reaction mixture was stirred for 5 hours at room temperature. Then the reaction mixture was carefully poured into a mixture of water (500 mL) and diethyl ether (100 mL) over 10 minutes and the mixture was stirred for 10 minutes. The reaction mixture was extracted with ether three times. The combined organic layers were washed with brine,dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (eluent;hexane) with small amount of neutral silica gel (5 g) to give allene 2. In case of synthesis of 2b, 2c, 2d, and 2e, the residue was purified with Kugelrohr before separation by column chromatography
  • 50
  • [ 100-43-6 ]
  • [ 1000-50-6 ]
  • 4-{2-[butyl(dimethyl)silyl]ethyl}pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
45% With magnesium In 1-methyl-pyrrolidin-2-one at 20℃; for 3h; Inert atmosphere; 4.2. General procedure for reductive silylation of vinylpyridines General procedure: Under the nitrogen atmosphere, to a 100 mL-four-necked flask charged with Mg turnings (0.36 g, 15 mmol) for Grignard reaction without pre-treatment, chlorotrialkylsilane (30 mmol) and dry NMP (20 mL), vinylpyridine (5 mmol) in NMP (10 mL) was added dropwise at 25 °C within 30 min and the reaction mixture was stirred for 3 h at room temperature. Subsequently, the mixture was carefully poured into a mixture of diethyl ether (50 mL) and saturated sodium bicarbonate solution (200 mL), and stirring was continued for 10 min. Then, the product was extracted with diethyl ether three times and the combined organic layer was washed with brine, dried over anhydrous magnesium sulfate overnight. Next, the solvent was evaporated under reduced pressure and the residue was finally purified by column chromatography.
  • 51
  • [ 109-04-6 ]
  • [ 1000-50-6 ]
  • 2-(butyldimethylsilyl)pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% Stage #1: 2-bromo-pyridine With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere; Stage #2: butyldimethylsilyl chloride In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere;
  • 52
  • [ 109-04-6 ]
  • [ 1000-50-6 ]
  • 2-(butyl(methyl)(pentyl)silyl)pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: n-butyllithium / hexane; tetrahydrofuran / 2 h / -78 °C / Inert atmosphere 1.2: -78 - 20 °C / Inert atmosphere 2.1: palladium diacetate; N-acetylglycine; p-benzoquinone; silver carbonate; sodium hydrogencarbonate / tetrahydrofuran / 48 h / 60 °C
  • 53
  • [ 1000-50-6 ]
  • [ 25555-57-1 ]
  • 3-[3,7-dimethylocta-2,6-diene]-2-hydroxy-6-pentyl-4-[t-butyldimethylsilyloxy]benzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 1H-imidazole In dichloromethane Inert atmosphere; E E. Synthesis of TBDMS-CBGA (3-[3,7-dimethylocta-2,6-diene]-2-hydroxy-6-pentyl -4-[t-butyldimeihylsilyloxy]benzoic acid) or 32 TBDMS-CBGA-ethyl ester (Ethyl-3-[3,7-dimethylocta-2,6-diene]-2-hydroxy-6-pentyl -4[t-butyldimethylsilyloxy]benzoate) To a cold stirring solution of 19 CBGA or 33 CBGA-ethyl ester in 34 DCM under an atmosphere of argon is added 35 7-butyldimethylsilyl chloride (1.0 eq.) and 36 imidazole. TLC is used to monitor reaction progress. The reaction is quenched upon completion by the addition of brine. The organic layer was separated and dried using anhydrous magnesium sulfate prior to purification and use. If CBGA-ethyl ester is used as the starting material, the product can be hydrolyzed to the corresponding acid, if necessary, prior to enzyme-catalyzed synthesis of the cannabinoid prodrug.
  • 54
  • [ 1000-50-6 ]
  • [ 62713-14-8 ]
  • [ 35153-45-8 ]
  • ethyl 3-butyldimethylsilyl-3-phenyl-3-trimethylsilylpropanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With magnesium In 1-methyl-pyrrolidin-2-one at 20℃; for 5h; Inert atmosphere;
  • 55
  • [ 1000-50-6 ]
  • [ 460-00-4 ]
  • butyl(4-fluorophenyl)dimethylsilane [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% Stage #1: 1-Bromo-4-fluorobenzene With magnesium; ethylene dibromide In tetrahydrofuran Inert atmosphere; Schlenk technique; Stage #2: butyldimethylsilyl chloride In tetrahydrofuran at 0 - 20℃; for 8h; Inert atmosphere; Schlenk technique;
  • 56
  • [ 1000-50-6 ]
  • [ 1493-13-6 ]
  • n-butyldimethylsilyl trifluoromethanesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
at 40℃; for 24h; Schlenk technique; Inert atmosphere;
  • 57
  • [ 1000-50-6 ]
  • (8-bromonaphthalen-1-yl)(butyl)dimethylsilane [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: 24 h / 40 °C / Schlenk technique; Inert atmosphere 2.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 °C / Schlenk technique; Inert atmosphere 2.2: 20 °C / Schlenk technique; Inert atmosphere
  • 58
  • [ 1000-50-6 ]
  • (E)-butyl(methyl)(naphthalen-1-yl)(styryl)silane [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: 24 h / 40 °C / Schlenk technique; Inert atmosphere 2.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 °C / Schlenk technique; Inert atmosphere 2.2: 20 °C / Schlenk technique; Inert atmosphere 3.1: tris-(dibenzylideneacetone)dipalladium(0); dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; lithium tert-butoxide / toluene / 24 h / 100 °C / Schlenk technique; Inert atmosphere
  • 59
  • [ 1000-50-6 ]
  • benzyl(butyl)(methyl)(naphthalen-1-yl)silane [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: 24 h / 40 °C / Schlenk technique; Inert atmosphere 2.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 °C / Schlenk technique; Inert atmosphere 2.2: 20 °C / Schlenk technique; Inert atmosphere 3.1: tris-(dibenzylideneacetone)dipalladium(0); dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; caesium carbonate / toluene / 24 h / 100 °C / Schlenk technique; Inert atmosphere
  • 60
  • [ 1000-50-6 ]
  • butyl(methyl)(naphthalen-1-yl)((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-methyl)silane [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: 24 h / 40 °C / Schlenk technique; Inert atmosphere 2.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 °C / Schlenk technique; Inert atmosphere 2.2: 20 °C / Schlenk technique; Inert atmosphere 3.1: tris-(dibenzylideneacetone)dipalladium(0); dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; caesium carbonate / toluene / 24 h / 100 °C / Schlenk technique; Inert atmosphere
  • 61
  • [ 1000-50-6 ]
  • [ 1001-52-1 ]
YieldReaction ConditionsOperation in experiment
96% With lithium aluminium tetrahydride; Tetraethylene glycol dimethyl ether at 20℃; Inert atmosphere;
  • 62
  • [ 1000-50-6 ]
  • [ 141-53-7 ]
  • C7H16O2Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With Tetraethylene glycol dimethyl ether at 20℃; Inert atmosphere;
  • 63
  • [ 1000-50-6 ]
  • [ 124-41-4 ]
  • [ 64712-50-1 ]
YieldReaction ConditionsOperation in experiment
94% With Tetraethylene glycol dimethyl ether at 80℃; for 48h; Inert atmosphere;
  • 64
  • [ 1000-50-6 ]
  • [ 20469-65-2 ]
  • (3,5-dimethoxyphenyl)(n-butyl)dimethylsilane [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% Stage #1: 1-bromo-3,5-dimethoxybenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: butyldimethylsilyl chloride In tetrahydrofuran; hexane at -78 - 20℃; for 3h; Inert atmosphere; 1.1 Step 1: Synthesis of butyl(3,5-dimethoxyphenyl)dimethylsilane Weigh 1-bromo-3,5-dimethoxybenzene (500mg, 2.3mmol) into a flask, add anhydrous tetrahydrofuran (10mL) under argon protection, The temperature in the low-temperature reactor was lowered to -78°C, and the n-butyl lithium n-hexane solution (1.60M, 4.3mL, 6.9mmol) was slowly added dropwise. The reaction was stirred at -78°C for half an hour, and then butyldimethylchlorosilane (1.04g, 6.9mmol) was slowly added dropwise. After stirring for 2 hours, it was moved to room temperature and stirred for 1 hour. A saturated aqueous solution of ammonium chloride (10 mL) was added to the reaction system to quench the reaction, and it was extracted three times with ethyl acetate. The organic phases were combined and washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated. Purification by silica gel column chromatography (ethyl acetate/petroleum ether = 2/98) gave a colorless oil (600 mg, yield 86%).
86% Stage #1: 1-bromo-3,5-dimethoxybenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: butyldimethylsilyl chloride In tetrahydrofuran; hexane at -78 - 20℃; for 3.5h; Inert atmosphere; 4.2.1 (3,5-Dimethoxyphenyl) (ethyl)dimethylsilane (12a) General procedure: To a stirred solution of 1-bromo-3,5-dimethoxybenzene (500mg, 2.3mmol) in THF (12mL) was slowly added a solution of n-BuLi in hexane (1.60M, 4.3mL, 6.9mmol) at-78°C under argon atmosphere. After 0.5h, ethylchlorodimethylsilane (1.04g, 6.9mmol) was slowly added into the mixture at-78°C over a period of 0.5h. After stirring at the same temperature for 2h, the mixture was allowed to warm to room temperature and stirred for an additional 1h. Saturated aqueous NH4Cl was added to quench the reaction and the mixture was extracted with EtOAc. The combined organic layers were washed with water and brine, then dried over Na2SO4. Volatiles were removed in vacuum and the residue was purified by silica chromatography (EtOAc/hexane=2/98) to give 12a as a colorless oil (600mg, yield: 80%).
  • 65
  • [ 1000-50-6 ]
  • (1'R,2'R)-4-(butyldimethylsilyl)-5'-methyl-2'-(prop-1-en-2-yl)-1',2',3',4'-tetrahydro-[1,1'-biphenyl]-2,6-diol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 1.2: 3 h / -78 - 20 °C / Inert atmosphere 2.1: boron tribromide / dichloromethane / 20 °C / Cooling with ice 3.1: toluene-4-sulfonic acid / toluene / 20 °C
Multi-step reaction with 3 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 1.2: 3.5 h / -78 - 20 °C / Inert atmosphere 2.1: boron tribromide / dichloromethane / -20 °C / Inert atmosphere 3.1: toluene-4-sulfonic acid / toluene / 20 °C
  • 66
  • [ 1000-50-6 ]
  • (6aR,10aR)-3-(butyldimethylsilyl)-9-hydroxymethyl-6,6-dimethyl-6a,7,10,10a-tetrahydro-6H-dibenzo[b,d]pyran-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 1.2: 3 h / -78 - 20 °C / Inert atmosphere 2.1: boron tribromide / dichloromethane / 20 °C / Cooling with ice 3.1: boron trifluoride diethyl etherate / dichloromethane / 2 h / -20 - 20 °C / Inert atmosphere 4.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 20 °C / Cooling with ice; Inert atmosphere
Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 1.2: 3.5 h / -78 - 20 °C / Inert atmosphere 2.1: boron tribromide / dichloromethane / -20 °C / Inert atmosphere 3.1: boron trifluoride diethyl etherate / dichloromethane / 2 h / -20 - 20 °C / Inert atmosphere 4.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
  • 67
  • [ 1000-50-6 ]
  • 3-(butyldimethylsilyl)-9-hydroxymethyl-6,6-dimethyl-6H-dibenzo[b,d]pyran-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 1.2: 3 h / -78 - 20 °C / Inert atmosphere 2.1: boron tribromide / dichloromethane / 20 °C / Cooling with ice 3.1: boron trifluoride diethyl etherate / dichloromethane / 2 h / -20 - 20 °C / Inert atmosphere 4.1: pyridine / 20 °C / Cooling with ice 5.1: sulfur / 0.67 h / 240 °C / Inert atmosphere 6.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 20 °C / Cooling with ice; Inert atmosphere
Multi-step reaction with 6 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 1.2: 3.5 h / -78 - 20 °C / Inert atmosphere 2.1: boron tribromide / dichloromethane / -20 °C / Inert atmosphere 3.1: boron trifluoride diethyl etherate / dichloromethane / 2 h / -20 - 20 °C / Inert atmosphere 4.1: pyridine / 0 - 20 °C 5.1: sulfur / 0.67 h / 250 °C / Inert atmosphere 6.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere
  • 68
  • [ 1000-50-6 ]
  • 1-(4-(butyldimethylsilyl)-2,6-dimethoxyphenyl)cyclohexan-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 1.2: 3 h / -78 - 20 °C / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / Inert atmosphere; Cooling with ice 2.2: 20 °C / Inert atmosphere
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 1.2: 3.5 h / -78 - 20 °C / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / Inert atmosphere 2.2: Inert atmosphere
  • 69
  • [ 1000-50-6 ]
  • butyl(4-cyclohexyl-3,5-dimethoxyphenyl)dimethylsilane [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 1.2: 3 h / -78 - 20 °C / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / Inert atmosphere; Cooling with ice 2.2: 20 °C / Inert atmosphere 3.1: trifluoroacetic acid; triethylsilane / dichloromethane / 1 h / 20 °C
Multi-step reaction with 3 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 1.2: 3.5 h / -78 - 20 °C / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / Inert atmosphere 2.2: Inert atmosphere 3.1: trifluoroacetic acid; triethylsilane / dichloromethane
  • 70
  • [ 1000-50-6 ]
  • 5-(butyldimethylsilyl)benzene-1,3-diol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 1.2: 3 h / -78 - 20 °C / Inert atmosphere 2.1: boron tribromide / dichloromethane / 20 °C / Cooling with ice
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 1.2: 3.5 h / -78 - 20 °C / Inert atmosphere 2.1: boron tribromide / dichloromethane / -20 °C / Inert atmosphere
  • 71
  • [ 1000-50-6 ]
  • (6aR,10aR)-3-(butyldimethylsilyl)-9-trimethylacetoxymethyl-6,6-dimethyl-6a,7,10,10a-tetrahydro-6H-dibenzo[b,d]pyran-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 1.2: 3 h / -78 - 20 °C / Inert atmosphere 2.1: boron tribromide / dichloromethane / 20 °C / Cooling with ice 3.1: boron trifluoride diethyl etherate / dichloromethane / 2 h / -20 - 20 °C / Inert atmosphere
Multi-step reaction with 3 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 1.2: 3.5 h / -78 - 20 °C / Inert atmosphere 2.1: boron tribromide / dichloromethane / -20 °C / Inert atmosphere 3.1: boron trifluoride diethyl etherate / dichloromethane / 2 h / -20 - 20 °C / Inert atmosphere
  • 72
  • [ 1000-50-6 ]
  • (6aR,10aR)-3-(butyldimethylsilyl)-9-trimethylacetoxymethyl-6,6-dimethyl-6a,7,10,10a-tetrahydro-6H-dibenzo[b,d]pyran-1-yl acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 1.2: 3 h / -78 - 20 °C / Inert atmosphere 2.1: boron tribromide / dichloromethane / 20 °C / Cooling with ice 3.1: boron trifluoride diethyl etherate / dichloromethane / 2 h / -20 - 20 °C / Inert atmosphere 4.1: pyridine / 20 °C / Cooling with ice
Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 1.2: 3.5 h / -78 - 20 °C / Inert atmosphere 2.1: boron tribromide / dichloromethane / -20 °C / Inert atmosphere 3.1: boron trifluoride diethyl etherate / dichloromethane / 2 h / -20 - 20 °C / Inert atmosphere 4.1: pyridine / 0 - 20 °C
  • 73
  • [ 1000-50-6 ]
  • 3-(butyldimethylsilyl)-9-trimethylacetoxymethyl-6,6-trimethyl-6H-dibenzo[b,d]pyran-1-yl acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 1.2: 3 h / -78 - 20 °C / Inert atmosphere 2.1: boron tribromide / dichloromethane / 20 °C / Cooling with ice 3.1: boron trifluoride diethyl etherate / dichloromethane / 2 h / -20 - 20 °C / Inert atmosphere 4.1: pyridine / 20 °C / Cooling with ice 5.1: sulfur / 0.67 h / 240 °C / Inert atmosphere
Multi-step reaction with 5 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 1.2: 3.5 h / -78 - 20 °C / Inert atmosphere 2.1: boron tribromide / dichloromethane / -20 °C / Inert atmosphere 3.1: boron trifluoride diethyl etherate / dichloromethane / 2 h / -20 - 20 °C / Inert atmosphere 4.1: pyridine / 0 - 20 °C 5.1: sulfur / 0.67 h / 250 °C / Inert atmosphere
  • 74
  • [ 1000-50-6 ]
  • [ 105-13-5 ]
  • (4-methoxybenzyloxy)dimethyl(n-butyl)silane [ No CAS ]
YieldReaction ConditionsOperation in experiment
113.3 mg With dmap; triethylamine at 20℃; for 1h;
  • 75
  • [ 1116-70-7 ]
  • [ 75-78-5 ]
  • [ 1000-50-6 ]
YieldReaction ConditionsOperation in experiment
95 %Spectr. With bis(η3-allyl-μ-chloropalladium(II)); DavePhos In 1,4-dioxane; hexane at 120℃; for 18h;
  • 76
  • [ 120-57-0 ]
  • [ 1000-50-6 ]
  • 1,3-dioxoisoindolin-2-yl 5-phenylpentanoate [ No CAS ]
  • C24H34O3Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
32 %Spectr. With chromium chloride; tetrabutylammonium perchlorate In N,N-dimethyl-formamide for 12h; Inert atmosphere; Electrochemical reaction;
  • 77
  • [ 1000-50-6 ]
  • [ 591-17-3 ]
  • [ 20171-66-8 ]
YieldReaction ConditionsOperation in experiment
100% Stage #1: 1-bromo-3-methylbenzene With n-butyllithium In tetrahydrofuran; hexane at -72℃; for 0.75h; Stage #2: butyldimethylsilyl chloride In tetrahydrofuran; hexane at -78 - 20℃;
  • 78
  • [ 1000-50-6 ]
  • [ 108-36-1 ]
  • C18H34Si2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% Stage #1: 1,3-dibromobenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: butyldimethylsilyl chloride In tetrahydrofuran; hexane at 20℃;
  • 79
  • [ 1000-50-6 ]
  • [ 626-39-1 ]
  • C24H48Si3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
48% Stage #1: 1,3,5-trisbromobenzene With n-butyllithium In tetrahydrofuran; hexane at -76℃; for 0.5h; Stage #2: butyldimethylsilyl chloride In tetrahydrofuran; hexane at 20℃;
  • 80
  • [ 1000-50-6 ]
  • 1-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)-4-iodobenzene [ No CAS ]
  • C17H24F6O2Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)-4-iodobenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: butyldimethylsilyl chloride In tetrahydrofuran; hexane at 20℃; for 2h; Inert atmosphere; general procedure of Method A General procedure: To a mixture of compound 30 (373 mg, 0.90 mmol)and dry THF(5.0 mL) was added n-BuLi in n-Hexane (1.6 M hexane solution, 0.75 mL, 1.20 mmol) dropwise under Ar atmosphere at -78. The mixture was stirred at -78 for 1 h. R1R2R3SiCl (3.0 mmol) was added and stirring at rt for 2 h. The reaction mixture was quenched with sat.NH4Cl, and the whole was extracted with EtOAc. The extract was successively washed with brine, and then dried over Na2SO4. The solvent was evaporated, andthe residue was purified by means of silica gel column chromatography (Hex-EtOAc, EA=9%) to give the mixture of 30a-e and reductant as colorless oil. The mixture was used in the next reaction without further purification.
Stage #1: 1-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)-4-iodobenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: butyldimethylsilyl chloride In tetrahydrofuran; hexane at 20℃; for 2h; Inert atmosphere; general procedure of Method A General procedure: To a mixture of compound 30 (373 mg, 0.90 mmol)and dry THF(5.0 mL) was added n-BuLi in n-Hexane (1.6 M hexane solution, 0.75 mL, 1.20 mmol) dropwise under Ar atmosphere at -78. The mixture was stirred at -78 for 1 h. R1R2R3SiCl (3.0 mmol) was added and stirring at rt for 2 h. The reaction mixture was quenched with sat.NH4Cl, and the whole was extracted with EtOAc. The extract was successively washed with brine, and then dried over Na2SO4. The solvent was evaporated, andthe residue was purified by means of silica gel column chromatography (Hex-EtOAc, EA=9%) to give the mixture of 30a-e and reductant as colorless oil. The mixture was used in the next reaction without further purification.
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