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Product Details of [ 4160-51-4 ]

CAS No. :4160-51-4 MDL No. :MFCD00027138
Formula : C11H14O2 Boiling Point : -
Linear Structure Formula :- InChI Key :JLCDSZXBELPBRD-UHFFFAOYSA-N
M.W : 178.23 Pubchem ID :77810
Synonyms :

Safety of [ 4160-51-4 ]

Signal Word:Warning Class:
Precautionary Statements:P280-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 4160-51-4 ]

* 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 [ 4160-51-4 ]

[ 4160-51-4 ] Synthesis Path-Downstream   1~100

  • 1
  • [ 106-31-0 ]
  • [ 100-66-3 ]
  • [ 4160-51-4 ]
YieldReaction ConditionsOperation in experiment
98% With trifluoroacetic acid at 20℃; for 1.5h; Conditions A (used in Table 3, top) General procedure: An oven-dried vial was charged with anisole 1a (0.75 mmol, 1.0 equiv), acetic anhydride 2a (1.5 mmol, 2.0 equiv) and TFA (0.8 mL). The reaction mixture was stirred at room temperature and monitored by TLC or GC-MS. The reaction typically took 1.5 h to complete. Upon completion, aqueous sodium hydrogen carbonate was added and the aqueous phase was extracted with ethyl acetate (3 x 20 mL). The combined organic layers were dried over Na2SO4 and concentrated. The crude product was purified by silica gel column chromatography to afford ketone product 3a. Alternatively, the product can also be obtained without workup: upon completion, the solvent was removed under reduced pressure and the residue was subjected to silica gel flash column chromatography.
93% With lithium perchlorate In nitromethane Ambient temperature;
73% With GALDEN(R) SV 135 In chlorobenzene at 90℃; for 1h;
With iodine
57 %Chromat. at 80℃; for 2h; 2 Preparation of 1-(4-methoxyphenyl)-1-butanone Example 2 Preparation of 1-(4-methoxyphenyl)-1-butanone Anisole (540 μl, 4.9 mmol) and butanoic acid anhydride (160 μl, 0.98 mmol) were mixed with 1-ethyl-3-methylimidazolium trifluoromethanesulfonate (1.5139 g, 5.82 mmol) at 80° C. during 2 h as in Example 1. The work-up was also analogous to the one described in Example 1 to give 114.0 mg of the title compound. Yield: 57% (calculated by GC with internal standard). Selectivity orto/para: 0/100.
With Amberlyst 15 In 1,2-dichloro-ethane at 80℃; for 10h; Inert atmosphere;

  • 2
  • [ 100-66-3 ]
  • [ 141-75-3 ]
  • [ 4160-51-4 ]
YieldReaction ConditionsOperation in experiment
87% In 1,2-dichloro-ethane at 80℃; for 3h;
84% With MoO4(AlCl2)2 In neat (no solvent) at 20℃; for 18h; Green chemistry; Friedel-Crafts Acylation Reaction General procedure: The Friedel-Crafts acylation of Anisole (1 g, 9.26 mmol)(Aldrich, 99.0%) with propionyl chloride (5 equiv.)(Aldrich, 99.0%) using the prepared MoO4(AlCl22(5 wt%, 10 mg) catalyst was carried out in a magneticallystirred two-necked round bottom flask fitted witha guard tube (CaCl2, activated at 150 C for 2 h. Thepresent reaction mixture stirred at room temperature up tothe completion of reaction. Reaction progress was monitoredby thin layer chromatography (TLC). After completionof the reaction, reaction mixture was filtered andsolid catalyst was separated out. The separated solid catalystcan be recycled in next attempt of Friedel-Craftsacylation reaction. The reaction mixture was washed withdichloromethane (DCM) and water, the same process wasdone triplicate and collected the organic layer. The organiclayer was then dried over anhydrous sodium sulfate andconcentrated on rotary evaporator and crude acylated productwas obtained and purified on column chromatography.
81% With aluminium trichloride In tetrachloromethane at 0℃; for 2h;
65% With aluminium trichloride In 1,2-dichloro-ethane at 0 - 20℃;
With carbon disulfide; titanium tetrachloride
With aluminium trichloride; Petroleum ether
With aluminium trichloride; Petroleum ether
With aluminium trichloride In 1,2-dichloro-ethane at 0 - 20℃;
With aluminum (III) chloride In dichloromethane at 20℃; for 2h;
With aluminum (III) chloride In dichloromethane at 0℃;
With aluminum (III) chloride In dichloromethane at 0 - 20℃; for 0.5h;
With aluminum (III) chloride In dichloromethane at 0℃; for 2h; Sealed tube; Inert atmosphere; Typical Procedure for Transformation of Arenes 1 into 5-Alkyl-1-aryltetrazoles 3: General procedure: To a solution ofcumene 1A (1.0 mmol, 120.0 mg) in CH2Cl2 (2.0 mL) in a 30 mL sealed tube was added acetyl chloride(1.2 mmol, 85.4 μL) at 0 °C. After flash with argon gas, the mixture was stirred for a few minutes.Anhydrous AlCl3 (1.2 mmol, 161.0 mg) was added and the obtained mixture was stirred for 2 h at 0 °C.Then, the reaction mixture was quenched with cooled water (1.0 mL) and stirred for 0.5 h. Afterremoval of the solvent under reduced pressure, MeOH (3.0 mL), NH2OHHCl (1.5 mmol, 107.0 mg), andK2CO3 (1.5 mmol, 207.0 mg) were added. After flash with argon gas, the obtained mixture was stirredfor 16 h at rt. After removal of the solvent under reduced pressure, toluene (3.0 mL), DPPA (2.5 mmol,0.54 mL), and DBU (3.5 mmol, 0.53 mL) were added to the residue. After flash with argon gas, themixture was warmed at 120 °C for 16 h. The mixture was cooled to rt and then, sat. NaHCO3 aq. (15.0mL) was added. The mixture was filtered through Celite, and the filtrate was extracted with AcOEt(20.0 mL ×3). The organic layer was dried over Na2SO4. After removal of the solvent under reducedpressure, the residue was purified by short column chromatography on silica gel (n-hexane/AcOEt,3:1-1:3) to afford 1-(4’-isopropylphenyl)-5-methyl-1H-tetrazole 3Aa in 60% yield (121.1 mg).

Reference: [1]Choudhary, Vasant R.; Jana, Suman K.; Patil, Nilesh S. [Tetrahedron Letters, 2002, vol. 43, # 6, p. 1105 - 1107]
[2]Jadhav, Arvind H.; Chinnappan, Amutha; Hiremath, Vishwanath; Seo, Jeong Gil [Journal of Nanoscience and Nanotechnology, 2015, vol. 15, # 10, p. 8243 - 8250]
[3]Adamska; Dabrowski; Dziabuszek [Molecular Crystals and Liquid Crystals (1969-1991), 1981, vol. 76, # 1-2, p. 93 - 99]
[4]Naoum, Fotini; Kasiotis, Konstantinos M.; Magiatis, Prokopios; Haroutounian, Serkos A. [Molecules, 2007, vol. 12, # 7, p. 1259 - 1273]
[5]Cullinane et al. [Journal of the Chemical Society, 1952, p. 376,4106]
[6]Stuart; Tallman [Journal of the American Chemical Society, 1943, vol. 65, p. 1579]
[7]Skraup; Nieten [Chemische Berichte, 1924, vol. 57, p. 1303]
[8]Stauffer; Coletta; Tedesco; Nishiguchi; Carlson; Sun; Katzenellenbogen; Katzenellenbogen [Journal of Medicinal Chemistry, 2000, vol. 43, # 26, p. 4934 - 4947]
[9]Location in patent: scheme or table Ling, Cui; Zheng, Zhibing; Jiang, Xian Cheng; Zhong, Wu; Li, Song [Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 17, p. 5123 - 5125]
[10]Location in patent: scheme or table Schaefer, Anja; Wellner, Anja; Gust, Ronald [ChemMedChem, 2011, vol. 6, # 5, p. 794 - 803]
[11]Ma, Yueyue; Lv, Jufeng; Liu, Chengyu; Yao, Xiantong; Yan, Guoming; Yu, Wei; Ye, Jinxing [Angewandte Chemie - International Edition, 2019, vol. 58, # 20, p. 6756 - 6760][Angew. Chem., 2019, vol. 131, p. 6828 - 6832,5]
[12]Shibasaki, Kaho; Togo, Hideo [Heterocycles, 2020, vol. 100, # 11, p. 1816 - 1830]
  • 3
  • [ 100-66-3 ]
  • [ 107-92-6 ]
  • [ 4160-51-4 ]
YieldReaction ConditionsOperation in experiment
92% With aluminum oxide; trifluoroacetic anhydride for 0.333333h; Ambient temperature;
82% With hydrothermally synthesized Nb2O5-WOx nanofiber crystal calcined in N2 at 139.84℃; for 3h; Inert atmosphere;
78% With methanesulfonic acid at 45℃; for 8h; 7 Preparation of 4-Methoxy phenyl butanone Methanesulfonic acid (MSA, 768 g), Butanoic acid (44g) and Anisole (108g) were charged into a 1 liter reaction flask. The mixture was stirred for 8hrs at 45°C. After completion of the reaction, the reaction mass was diluted with water and product and unreacted Anisole was extracted using Toluene. The Toluene layer was distilled to recover 55g of unreacted Anisoleand obtain 68g of 4-Methoxy phenyl butanone (GC purity > 98%, yield 129 w/w% on Anisole consumed). The aqueous layer was distilled to recover 728g of MSA (purity > 98%) which was reused in subsequent batches.
With PPA
With Chloroacetic anhydride at 165 - 180℃;
87 % Turnov. With aluminium dodecatungsten phosphate at 120℃; for 5h;
With silica gel supported aluminium trichloride at 80℃; for 1.5h; regioselective reaction;
74 %Chromat. With pyrographite at 200℃; for 0.5h; Microwave irradiation; Sealed tube;
With cross-linked polystyrene-supported aluminum triflate at 80℃; for 2.7h; Neat (no solvent); regioselective reaction;

  • 5
  • [ 4160-51-4 ]
  • [ 39905-81-2 ]
YieldReaction ConditionsOperation in experiment
76% With silica gel; acetyl chloride; zinc(II) chloride In 1,2-dichloro-ethane at 30℃; for 0.5h;
With iron(III) chloride; butyryl chloride
  • 6
  • [ 201230-82-2 ]
  • [ 696-62-8 ]
  • [ 107-08-4 ]
  • [ 4160-51-4 ]
YieldReaction ConditionsOperation in experiment
90% With copper; zinc In tetrahydrofuran at 50℃; for 22h;
  • 7
  • [ 69638-92-2 ]
  • [ 100-66-3 ]
  • [ 4160-51-4 ]
YieldReaction ConditionsOperation in experiment
53% In dichloromethane for 24h; Ambient temperature;
  • 8
  • [ 84858-88-8 ]
  • [ 13404-83-6 ]
  • [ 700-12-9 ]
  • [ 4160-51-4 ]
YieldReaction ConditionsOperation in experiment
100% With methoxybenzene Heating;
  • 9
  • [ 345317-87-5 ]
  • [ 4160-51-4 ]
YieldReaction ConditionsOperation in experiment
26% With sodium hydride In tetrahydrofuran for 3.5h; Heating;
  • 10
  • [ 4160-51-4 ]
  • [ 18272-84-9 ]
YieldReaction ConditionsOperation in experiment
83% With potassium hydroxide; hydrazine hydrate In diethylene glycol for 3h; Heating;
  • 11
  • [ 24165-60-4 ]
  • (E)-1-(4-methoxyphenyl)pent-1-en-3-ol [ No CAS ]
  • [ 4160-51-4 ]
YieldReaction ConditionsOperation in experiment
1: 44.5 mg 2: 14 mg In water at 90 - 100℃; for 1.5h;
  • 12
  • [ 7152-03-6 ]
  • [ 4160-51-4 ]
YieldReaction ConditionsOperation in experiment
87% With trichlorosilane at 23℃; Irradiation;
60% With bis(1,5-cyclooctadiene)nickel (0); bathophenanthroline In methanol at 60℃; for 24h;
  • 13
  • [ 608-68-4 ]
  • [ 4160-51-4 ]
  • [ 306972-70-3 ]
YieldReaction ConditionsOperation in experiment
69% With methanesulfonic acid; trimethyl orthoformate at 95℃; for 120h;
  • 14
  • [ 7464-46-2 ]
  • [ 4160-51-4 ]
  • [ 71526-44-8 ]
YieldReaction ConditionsOperation in experiment
95% With lithium hexamethyldisilazane In tetrahydrofuran at 20℃; for 1.5h;
  • 15
  • [ 4160-51-4 ]
  • [ 97060-29-2 ]
YieldReaction ConditionsOperation in experiment
77% With N-tert-butyl benzenesulfinimidoyl chloride; lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 0.5h;
75% With oxygen; palladium diacetate; trifluoroacetic acid In dimethyl sulfoxide at 80℃; for 10h; Sealed tube;
  • 16
  • [ 2043-61-0 ]
  • [ 4160-51-4 ]
  • [ 440368-69-4 ]
YieldReaction ConditionsOperation in experiment
86% With titanium tetrachloride; triethylamine
  • 17
  • [ 93-04-9 ]
  • [ 141-75-3 ]
  • [ 4160-51-4 ]
YieldReaction ConditionsOperation in experiment
80% With Si-MCM-41 supported gallium oxide; water In 1,2-dichloro-ethane at 80℃; for 3h;
  • 18
  • [ 874-90-8 ]
  • [ 4160-51-4 ]
  • 5-ethyl-2,4,6-tri-(4'-methoxyphenyl)pyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With trifluoromethylsulfonic anhydride In 1,2-dichloro-ethane at 20℃; for 24h;
  • 19
  • [ 100-66-3 ]
  • [ 141-75-3 ]
  • [ 13404-83-6 ]
  • [ 4160-51-4 ]
YieldReaction ConditionsOperation in experiment
In chlorobenzene at 90℃; for 4h;
  • 20
  • [ 4160-51-4 ]
  • 1-(4-methoxyphenyl)butan-1-one oxime [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With hydroxylamine hydrochloride; potassium carbonate In ethanol Heating;
With hydroxylamine hydrochloride; potassium carbonate In methanol at 20℃; for 16h; Inert atmosphere; Typical Procedure for Transformation of Arenes 1 into 5-Alkyl-1-aryltetrazoles 3: General procedure: To a solution ofcumene 1A (1.0 mmol, 120.0 mg) in CH2Cl2 (2.0 mL) in a 30 mL sealed tube was added acetyl chloride(1.2 mmol, 85.4 μL) at 0 °C. After flash with argon gas, the mixture was stirred for a few minutes.Anhydrous AlCl3 (1.2 mmol, 161.0 mg) was added and the obtained mixture was stirred for 2 h at 0 °C.Then, the reaction mixture was quenched with cooled water (1.0 mL) and stirred for 0.5 h. Afterremoval of the solvent under reduced pressure, MeOH (3.0 mL), NH2OHHCl (1.5 mmol, 107.0 mg), andK2CO3 (1.5 mmol, 207.0 mg) were added. After flash with argon gas, the obtained mixture was stirredfor 16 h at rt. After removal of the solvent under reduced pressure, toluene (3.0 mL), DPPA (2.5 mmol,0.54 mL), and DBU (3.5 mmol, 0.53 mL) were added to the residue. After flash with argon gas, themixture was warmed at 120 °C for 16 h. The mixture was cooled to rt and then, sat. NaHCO3 aq. (15.0mL) was added. The mixture was filtered through Celite, and the filtrate was extracted with AcOEt(20.0 mL ×3). The organic layer was dried over Na2SO4. After removal of the solvent under reducedpressure, the residue was purified by short column chromatography on silica gel (n-hexane/AcOEt,3:1-1:3) to afford 1-(4’-isopropylphenyl)-5-methyl-1H-tetrazole 3Aa in 60% yield (121.1 mg).
  • 21
  • [ 141-75-3 ]
  • [ 98-86-2 ]
  • [ 39905-81-2 ]
  • [ 4160-51-4 ]
YieldReaction ConditionsOperation in experiment
1: 49% 2: 43% at 25℃;
  • 22
  • C15H24N2O [ No CAS ]
  • [ 4160-51-4 ]
YieldReaction ConditionsOperation in experiment
83.7 mg With hydrogenchloride In tetrahydrofuran; methanol at 20℃; for 3h;
  • 24
  • [ 33397-21-6 ]
  • [ 141-75-3 ]
  • [ 4160-51-4 ]
YieldReaction ConditionsOperation in experiment
65% With triethylamine In 1,4-dioxane at 80℃; for 3h;
  • 25
  • [ 4160-51-4 ]
  • (1R)-1-butyl-1-(4-methoxyphenyl)amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: 82 percent / hydroxylamine hydrochloride; K2CO3 / ethanol / Heating 2.1: NaH / dimethylformamide / 0 °C 2.2: 80 percent / dimethylformamide / 0 - 20 °C 3.1: BH3*THF; (S)-proline (R)-1,1'-bi(2-naphthyl)dioxyboryl ester / tetrahydrofuran / 48 h / 0 - 5 °C 3.2: aq. HCl / tetrahydrofuran
Multi-step reaction with 3 steps 1.1: titanium(IV) tetraethanolate / neat (no solvent) / 4 h / 72 °C / Inert atmosphere 2.1: 2-Amino-2-methyl-1-propanol; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 / isopropyl alcohol / 0.25 h / 50 °C / Inert atmosphere; Molecular sieve 2.2: 2 h / 50 °C / Inert atmosphere; Molecular sieve 3.1: hydrogenchloride / methanol; diethyl ether / 3 h / 0 - 20 °C / Inert atmosphere
  • 26
  • [ 4160-51-4 ]
  • [ 381229-27-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: 78 percent / Br2 / diethyl ether / 0.5 h 2.1: KHMDS / tetrahydrofuran; toluene / 1 h / -78 °C 2.2: 60 percent / tetrahydrofuran; toluene / -78 - 20 °C
  • 27
  • [ 4160-51-4 ]
  • [ 381229-39-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: 78 percent / Br2 / diethyl ether / 0.5 h 2.1: KHMDS / tetrahydrofuran; toluene / 1 h / -78 °C 2.2: 60 percent / tetrahydrofuran; toluene / -78 - 20 °C 3.1: 42 percent / TsOH*H2O / toluene / Heating
  • 28
  • [ 4160-51-4 ]
  • 4-(3-ethyl-4,5-diphenyl-furan-2-yl)-phenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: 78 percent / Br2 / diethyl ether / 0.5 h 2.1: KHMDS / tetrahydrofuran; toluene / 1 h / -78 °C 2.2: 60 percent / tetrahydrofuran; toluene / -78 - 20 °C 3.1: 42 percent / TsOH*H2O / toluene / Heating 4.1: 55 percent / BF3*SMe2 / CH2Cl2 / 20 °C
  • 29
  • [ 4160-51-4 ]
  • [ 381229-23-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: 78 percent / Br2 / diethyl ether / 0.5 h 2.1: KHMDS / tetrahydrofuran; toluene / -78 - 20 °C 2.2: 81.4 percent / tetrahydrofuran; toluene / 1.5 h / -78 °C
  • 30
  • [ 4160-51-4 ]
  • [ 381229-25-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: 78 percent / Br2 / diethyl ether / 0.5 h 2.1: KHDMS / tetrahydrofuran; toluene / 1 h / -78 °C 2.2: 96 percent / tetrahydrofuran; toluene / -78 - 20 °C
  • 31
  • [ 4160-51-4 ]
  • [ 381229-35-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: 78 percent / Br2 / diethyl ether / 0.5 h 2.1: KHMDS / tetrahydrofuran; toluene / -78 - 20 °C 2.2: 81.4 percent / tetrahydrofuran; toluene / 1.5 h / -78 °C 3.1: 88 percent / TsOH*H2O / toluene / Heating
  • 32
  • [ 4160-51-4 ]
  • [ 381229-37-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: 78 percent / Br2 / diethyl ether / 0.5 h 2.1: KHDMS / tetrahydrofuran; toluene / 1 h / -78 °C 2.2: 96 percent / tetrahydrofuran; toluene / -78 - 20 °C 3.1: 95 percent / TsOH*H2O / toluene / Heating
  • 33
  • [ 4160-51-4 ]
  • C24H20O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: 78 percent / Br2 / diethyl ether / 0.5 h 2.1: KHDMS / tetrahydrofuran; toluene / 1 h / -78 °C 2.2: 96 percent / tetrahydrofuran; toluene / -78 - 20 °C 3.1: 95 percent / TsOH*H2O / toluene / Heating 4.1: 93 percent / BF3*SMe2 / CH2Cl2 / 20 °C
  • 34
  • [ 4160-51-4 ]
  • C24H20O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: 78 percent / Br2 / diethyl ether / 0.5 h 2.1: KHMDS / tetrahydrofuran; toluene / -78 - 20 °C 2.2: 81.4 percent / tetrahydrofuran; toluene / 1.5 h / -78 °C 3.1: 88 percent / TsOH*H2O / toluene / Heating 4.1: 94 percent / BF3*SMe2 / CH2Cl2 / 20 °C
  • 35
  • [ 4160-51-4 ]
  • [ 381229-20-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: 78 percent / Br2 / diethyl ether / 0.5 h 2.1: KHMDS / tetrahydrofuran; toluene / 1 h / -78 °C 2.2: 80 percent / tetrahydrofuran; toluene / -78 - 20 °C
  • 36
  • [ 4160-51-4 ]
  • 3-ethyl-2,4,5-tris(4-methoxyphenyl)furan [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: 78 percent / Br2 / diethyl ether / 0.5 h 2.1: KHMDS / tetrahydrofuran; toluene / 1 h / -78 °C 2.2: 80 percent / tetrahydrofuran; toluene / -78 - 20 °C 3.1: 70 percent / TsOH*H2O / toluene / Heating
  • 37
  • [ 4160-51-4 ]
  • C24H20O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: 78 percent / Br2 / diethyl ether / 0.5 h 2.1: KHMDS / tetrahydrofuran; toluene / 1 h / -78 °C 2.2: 80 percent / tetrahydrofuran; toluene / -78 - 20 °C 3.1: 70 percent / TsOH*H2O / toluene / Heating 4.1: 93 percent / BF3*SMe2 / CH2Cl2 / 20 °C
  • 38
  • [ 4160-51-4 ]
  • C23H20N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 95 percent / LHMDS / tetrahydrofuran / 1.5 h / 20 °C 2: 87 percent / tetrahydrofuran; dimethylformamide / Heating 3: 54 percent / BBr3 / CH2Cl2 / -78 - 20 °C
  • 39
  • [ 4160-51-4 ]
  • 4-[1,3-bis(4-hydroxyphenyl)-4-ethylpyrazol-5-yl]phenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 95 percent / LHMDS / tetrahydrofuran / 1.5 h / 20 °C 2: 66 percent / tetrahydrofuran; dimethylformamide / Heating 3: 98 percent / BBr3 / CH2Cl2 / -78 - 20 °C
  • 40
  • [ 4160-51-4 ]
  • [ 234093-24-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 95 percent / LHMDS / tetrahydrofuran / 1.5 h / 20 °C 2: 87 percent / tetrahydrofuran; dimethylformamide / Heating
  • 41
  • [ 4160-51-4 ]
  • [ 234093-26-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 95 percent / LHMDS / tetrahydrofuran / 1.5 h / 20 °C 2: 66 percent / tetrahydrofuran; dimethylformamide / Heating
  • 42
  • [ 4160-51-4 ]
  • (2E,4E)-5-(4-Methoxy-phenyl)-octa-2,4-dienoic acid ((R)-1-methyl-4-pyridin-3-yl-butyl)-amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 2: 2.) NaOH / 1.) CH2Cl2, room temperature, 3 d, 2.) MeOH, H2O, reflux, 30 min 3: 68 percent / DCC / CH2Cl2 / 1.) 0-5 deg C, 60 min, 2.) room temperature, overnight 4: 73 percent / tetrahydrofuran / 1.) room temperature, overnight, 2.) reflux, 3 h
  • 43
  • [ 4160-51-4 ]
  • [ 120554-73-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 2: 2.) NaOH / 1.) CH2Cl2, room temperature, 3 d, 2.) MeOH, H2O, reflux, 30 min 3: 68 percent / DCC / CH2Cl2 / 1.) 0-5 deg C, 60 min, 2.) room temperature, overnight
  • 44
  • [ 4160-51-4 ]
  • [ 82938-18-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 1) NaH / 1) THF, <5 degC, 2) 60 degC, 6h 2: 79 percent / LAH / diethyl ether / 3 h / 0 °C 3: 40 percent / diethyl azodicarboxylate, triphenylphosphine / tetrahydrofuran / 18 h / Ambient temperature 4: 58 percent / NaBH4 / aq. ethanol / 0 °C / 1) addition of 2N HCl in 15min intervalls over 5h 2) pH 3, 1h 5: 34 percent / PTS / benzene / 0.75 h / Heating
  • 45
  • [ 4160-51-4 ]
  • [ 82938-19-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 1) NaH / 1) THF, <5 degC, 2) 60 degC, 6h 2: 79 percent / LAH / diethyl ether / 3 h / 0 °C 3: 40 percent / diethyl azodicarboxylate, triphenylphosphine / tetrahydrofuran / 18 h / Ambient temperature 4: 58 percent / NaBH4 / aq. ethanol / 0 °C / 1) addition of 2N HCl in 15min intervalls over 5h 2) pH 3, 1h 5: 34 percent / PTS / benzene / 0.75 h / Heating 6: 40 percent / H2 / PtO2, acetic acid / ethanol / 48 h / 3102.9 Torr
  • 46
  • [ 4160-51-4 ]
  • [ 6465-62-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: (i) Et2O, (ii) H2SO4 2: H2 / Pd-C / ethanol 3: aq. HBr / acetic acid 4: HNO3 / CCl4
  • 47
  • [ 4160-51-4 ]
  • [ 17473-32-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: (i) Et2O, (ii) TsOH 2: H2 / Pd-C / ethanol 3: aq. HBr / acetic acid 4: HNO3 / CCl4
  • 48
  • [ 4160-51-4 ]
  • [ 17473-36-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: (i) Et2O, (ii) TsOH 2: H2 / Pd-C / ethanol 3: aq. HBr / acetic acid 4: HNO3 / CCl4
  • 49
  • [ 4160-51-4 ]
  • [ 31254-28-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: (i) Mg, Et2O, (ii) /BRN= 908286/ 3: KOH / propan-2-ol
  • 50
  • [ 4160-51-4 ]
  • [ 56933-74-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: (i) Mg, Et2O, (ii) /BRN= 908286/ 3: KOH / propan-2-ol 4: TsOH / benzene
  • 51
  • [ 4160-51-4 ]
  • 2-Aethyl-6β-methyl-3-(p-hydroxyphenyl)-trans-bicyclo<4.3.0>non-2-en-7β-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: (i) Mg, Et2O, (ii) /BRN= 908286/ 3: KOH / propan-2-ol 4: TsOH / benzene 5: NaBH4 / ethanol 6: H2 / Pd-C / ethanol 7: KOH, N2H4 / bis-(2-hydroxy-ethyl) ether
  • 52
  • [ 4160-51-4 ]
  • 2-Aethyl-6β-methyl-3-(p-methoxyphenyl)-trans-bicyclo<4.3.0>non-2-en-7β-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: (i) Mg, Et2O, (ii) /BRN= 908286/ 3: KOH / propan-2-ol 4: TsOH / benzene 5: NaBH4 / ethanol 6: H2 / Pd-C / ethanol
  • 53
  • [ 4160-51-4 ]
  • 1-Hydroxy-2-methyl-2-<3-(p-methoxyphenyl)-2-hexenyl>-cyclopentan-3-on [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: (i) Mg, Et2O, (ii) /BRN= 908286/ 3: KOH / propan-2-ol 4: Li<AlH(OtBu)3> / tetrahydrofuran
  • 54
  • [ 4160-51-4 ]
  • 2α-Aethyl-3α-(p-hydroxyphenyl)-6β-methyl-trans-bicyclo<4.3.0>nonan-7β-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: (i) Mg, Et2O, (ii) /BRN= 908286/ 3: KOH / propan-2-ol 4: TsOH / benzene 5: NaBH4 / ethanol 6: H2 / Pd-C / ethanol 7: KOH, N2H4 / bis-(2-hydroxy-ethyl) ether
  • 55
  • [ 4160-51-4 ]
  • 2α-Aethyl-3β-(p-hydroxyphenyl)-6β-methyl-trans-bicyclo<4.3.0>nonan-7β-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: (i) Mg, Et2O, (ii) /BRN= 908286/ 3: KOH / propan-2-ol 4: TsOH / benzene 5: NaBH4 / ethanol 6: H2 / Pd-C / ethanol 7: K, liq. NH3 / diethyl ether; dioxane 8: KOH, N2H4 / bis-(2-hydroxy-ethyl) ether
  • 56
  • [ 4160-51-4 ]
  • 2β-Aethyl-3β-(p-hydroxyphenyl)-6β-methyl-trans-bicyclo<4.3.0>nonan-7β-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: (i) Mg, Et2O, (ii) /BRN= 908286/ 3: KOH / propan-2-ol 4: TsOH / benzene 5: NaBH4 / ethanol 6: H2 / Pd-C / ethanol 7: KOH, N2H4 / bis-(2-hydroxy-ethyl) ether
Multi-step reaction with 7 steps 1: (i) Mg, Et2O, (ii) /BRN= 908286/ 3: KOH / propan-2-ol 4: TsOH / benzene 5: NaBH4 / ethanol 6: H2 / Pd-C / ethanol 7: KOH, N2H4 / bis-(2-hydroxy-ethyl) ether
  • 57
  • [ 4160-51-4 ]
  • 2α-Aethyl-3α-(p-methoxyphenyl)-6β-methyl-trans-bicyclo<4.3.0>nonan-7β-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: (i) Mg, Et2O, (ii) /BRN= 908286/ 3: KOH / propan-2-ol 4: TsOH / benzene 5: NaBH4 / ethanol 6: H2 / Pd-C / ethanol
  • 58
  • [ 4160-51-4 ]
  • 2α-Aethyl-3β-(p-methoxyphenyl)-6β-methyl-trans-bicyclo<4.3.0>nonan-7β-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: (i) Mg, Et2O, (ii) /BRN= 908286/ 3: KOH / propan-2-ol 4: TsOH / benzene 5: NaBH4 / ethanol 6: H2 / Pd-C / ethanol 7: K, liq. NH3 / diethyl ether; dioxane
  • 59
  • [ 4160-51-4 ]
  • 2β-Aethyl-3β-(p-methoxyphenyl)-6β-methyl-trans-bicyclo<4.3.0>nonan-7β-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: (i) Mg, Et2O, (ii) /BRN= 908286/ 3: KOH / propan-2-ol 4: TsOH / benzene 5: NaBH4 / ethanol 6: H2 / Pd-C / ethanol
Multi-step reaction with 6 steps 1: (i) Mg, Et2O, (ii) /BRN= 908286/ 3: KOH / propan-2-ol 4: TsOH / benzene 5: NaBH4 / ethanol 6: H2 / Pd-C / ethanol
  • 60
  • [ 4160-51-4 ]
  • 2-Aethyl-6β-methyl-3-(p-methoxyphenyl)-bicyclo<4.3.0>nona-2.9-dien-7β-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: (i) Mg, Et2O, (ii) /BRN= 908286/ 3: KOH / propan-2-ol 4: TsOH / benzene 5: NaBH4 / ethanol
  • 61
  • [ 7020-80-6 ]
  • [ 814-49-3 ]
  • [ 4160-51-4 ]
  • [ 120553-85-7 ]
  • (Z)-3-(4-Methoxyphenyl)-2-hexenal [ No CAS ]
YieldReaction ConditionsOperation in experiment
With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane; oxalic acid 177 Preparation of (E)-3-(4-methoxyphenyl)-2-hexenal and (Z)-3-(4-methoxyphenyl)-2-hexenal EXAMPLE 177 Preparation of (E)-3-(4-methoxyphenyl)-2-hexenal and (Z)-3-(4-methoxyphenyl)-2-hexenal The compounds were prepared according to the procedure described in Example 84 except that the reaction was worked up after 3 days. The following reagents were used: 4'-methoxybutyrophenone (17.8 g), diisopropylamine (32.2 mL), 1.6M n-butyl lithium in hexane (143 mL), acetaldehyde N-tert-butylimine (14.75 mL), diethyl chlorophosphonate (16.6 mL) and tetrahydrofuran (200 mL). The work up, varied only in that the oxalic acid hydrolysis was run for 3 days at room temperature, furnished 21.1 g of crude product containing (E)-3-(4-methoxyphenyl)-2-hexenal and (Z)-3-(4-methoxyphenyl)-2-hexenal in an E/Z ratio of ~3:4. The mixture was separated by HPLC (ether-hexane; 1:7.5) to give 8.2 g of the less polar (Z)-3-(4-methoxyphenyl)-2-hexenal as an oil and 6.0 g of its isomer, (E)-3-(4-methoxyphenyl)-2-hexenal, as an oil.
  • 62
  • [ 4160-51-4 ]
  • [ 71526-44-8 ]
YieldReaction ConditionsOperation in experiment
In [(CH3)2Si]2NLi 1 5.1.2.46 Synthesis of 4-[1-(2,4-dimethylphenyl)-4-ethyl-5-(4-hydroxyphenyl)pyrazol-3-yl]phenol Step 1: To a solution of 4'-methoxybutyrylphenone (1.0 equiv.) in TBF at -78° C. was added dropwise 1.5 equiv. of [(CH3)2Si]2NLi. The solution was stirred for 1 h at -78° C., followed by addition of 1.2 equiv. of p-aisoyl chloride. The reaction mixture was stirred for 10 min at -78° C. and then for 22 h at rt, acidified with 10% citric acid, and extracted with EtOAc. The combined organic layers were washed with water and dried over Na2SO4. Removal of solvent in vacuo provided a crude solid which was purified by flash chromatography (CH2Cl2) to give 1,3-bis(4-methoxyphenyl)-2-ethylpropane-1,3-dione.
  • 63
  • [(CH3)2Si]2NLi [ No CAS ]
  • [ 100-07-2 ]
  • [ 4160-51-4 ]
  • [ 71526-44-8 ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran 1 5.1.2.88 Synthesis of 4-{4-ethyl-5-(4-hydroxyphenyl-1-[(4-hydroxyphenyl)methyl]pyrazol-3-yl}phenol Step 1: To a solution of 4'-methoxybutyryl phenone (1.0 equiv.) in THF at -78° C. was added dropwise 1.5 equiv. of [(CH3)2Si]2NLi. The solution was stirred for 1 h at -78° C., followed by addition of 1.2 equiv. of p-anisoyl chloride. The reaction mixture was stirred for 10 min at -78° C. and then for 22 h at rt, acidified with 10% citric acid, and extracted with EtOAc. The combined organic layers were washed with water and dried over Na2SO4. Removal of solvent in vacuo provided a crude solid which was purified by flash chromatography (CH2Cl2) to give 1,3-bis(4-methoxyphenyl)-2-ethylpropane-1,3-dione.
  • 64
  • C13H18O2 [ No CAS ]
  • [ 4160-51-4 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; water In diethyl ether at 20℃; for 1h; Inert atmosphere;
With hydrogenchloride In acetone at 20℃; for 1h;
  • 65
  • [ 104-92-7 ]
  • [ 123-72-8 ]
  • [ 4160-51-4 ]
YieldReaction ConditionsOperation in experiment
81% With pyrrolidine; 1,3-bis-(diphenylphosphino)propane; bis(dibenzylideneacetone)-palladium(0) In N,N-dimethyl-formamide at 115℃; for 6h; Molecular sieve;
  • 66
  • [ 110480-91-6 ]
  • [ 4160-51-4 ]
YieldReaction ConditionsOperation in experiment
92% With magnesium sulphate; vanadyl(IV) sulphate pentahydrate; 4-nitrophenyl(phenyl)methanol; 4,4'-di-tert-butyl-2,2'-bipyridine In water at 0 - 90℃; for 120h; 4.6 Oxidation of alcohols under open-air atmosphere General procedure: VOSO4·5H2O (126.5 mg, 0.5 mmol), 4,4′-di-tert-butyl-2,2′-bipyridyl (268.4 mg, 1 mmol), and p-nitrobenzhydrol (229.3 mg, 0.05 mmol) were placed in a 100 mL round-bottomed flask, and then water (50 mL) was added. Next, the mixture was stirred, and then anhydrous MgSO4 (18.06 g, 150 mmol) was slowly added into the mixture (cooling by ice water). After that, substrate (10 mmol) was added into the mixture at room temperature, and the mixture was stirred at 90 °C for the appropriate time under open-air atmosphere. After the reaction, the mixture was extracted with ethyl acetate and dried over anhydrous MgSO4. The extracts were concentrated in vacuo. Purification of the products was carried out by silica gel column chromatography using hexane and diethyl ether as eluent to afford the analytically pure ketones. In Table 7 (entries 3, 7, and 8), crude products were purified by recrystallization with ethyl acetate in refrigerator, afforded analytically pure ketones. The product was identified by comparison with the commercially available sample using 1H NMR spectroscopy.
76% With Candida antarctica lipase B immobilized; dihydrogen peroxide In water at 60℃; for 10h; Ionic liquid; Enzymatic reaction; chemoselective reaction;
With pyridinium chlorochromate In dichloromethane at 20℃; for 3h;
  • 67
  • [ 18272-84-9 ]
  • [ 4160-51-4 ]
YieldReaction ConditionsOperation in experiment
44% With manganese(II) chloride tetrahydrate; water; 3-chloro-benzenecarboperoxoic acid; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine In acetonitrile at 0℃; for 0.333333h; chemoselective reaction;
  • 68
  • [ 623-12-1 ]
  • [ 123-72-8 ]
  • [ 4160-51-4 ]
YieldReaction ConditionsOperation in experiment
60% With pyrrolidine; 2-(di-tert-butylphosphino)-1-(2-methoxyphenyl)-1H-pyrrole; bis(dibenzylideneacetone)-palladium(0) In N,N-dimethyl acetamide at 140℃; for 4h; Inert atmosphere; Molecular sieve;
  • 69
  • [ 696-62-8 ]
  • [ 122-57-6 ]
  • [ 2132-80-1 ]
  • [ 61866-52-2 ]
  • [ 76217-07-7 ]
  • [ 273754-93-1 ]
  • [ 4160-51-4 ]
YieldReaction ConditionsOperation in experiment
62% With bis(acetato)bis(triphenylphosphine)palladium(0); tributyl-amine; tetra-(n-butyl)ammonium iodide; trifluoroacetic acid In N,N-dimethyl-formamide at 70℃; for 12h;
  • 70
  • [ 98-64-6 ]
  • [ 4160-51-4 ]
  • [ 1263313-25-2 ]
YieldReaction ConditionsOperation in experiment
76% With palladium(II) bis(trifluoromethanesulfonate) dihydrate; 1-fluoro-2,4,6-trimethylpyridinium trifluoromethanesulfonate In dichloromethane at 80℃; for 8h;
  • 71
  • [ 102-82-9 ]
  • [ 696-62-8 ]
  • [ 4160-51-4 ]
YieldReaction ConditionsOperation in experiment
73% With dichloro bis(acetonitrile) palladium(II); tetrabutylammomium bromide; water; zinc(II) oxide In dimethyl sulfoxide at 100℃; for 16h;
  • 72
  • [ 696-62-8 ]
  • [ 4383-27-1 ]
  • [ 4160-51-4 ]
YieldReaction ConditionsOperation in experiment
50% With dichloro bis(acetonitrile) palladium(II); tetrabutylammomium bromide; water; zinc(II) oxide In dimethyl sulfoxide at 100℃; for 48h;
  • 73
  • [ 696-62-8 ]
  • [ 123-72-8 ]
  • [ 4160-51-4 ]
YieldReaction ConditionsOperation in experiment
60% With nickel(II) iodide; potassium phosphate; tetrakis(tetrabutylammonium)decatungstate(VI); 4,4'-di-tert-butyl-2,2'-bipyridine In acetonitrile at 20℃; for 4h; Schlenk technique; Inert atmosphere; Irradiation;
58% With dichloro bis(acetonitrile) palladium(II); tetrabutylammomium bromide; dibutylamine; zinc(II) oxide In dimethyl sulfoxide at 100℃; for 16h;
  • 74
  • [ 84132-74-1 ]
  • [ 17113-31-4 ]
  • [ 97060-29-2 ]
  • [ 4160-51-4 ]
YieldReaction ConditionsOperation in experiment
1: 53% 2: 11% 3: 4% With Shvo's catalyst In acetone at 65℃; for 29h; Inert atmosphere;
  • 75
  • [ 1415455-15-0 ]
  • [ 4160-51-4 ]
YieldReaction ConditionsOperation in experiment
86% With 2,2,6,6-tetramethyl-piperidine; n-butyllithium In tetrahydrofuran; hexane at -20℃; for 12h; Inert atmosphere; General procedure for the deprotection of 1,3-dioxolanes promoted by lithium 2,2,6,6-tetramethylpiperidide (Table 2 and Table 3) General procedure: To a solution of 2,2,6,6-tetramethylpiperidine (TMP) (0.34 mL, 2.00 mmol, 4.0 equiv.) in THF (4 mL) was added n-BuLi (2.4 M in hexane, 0.83 mL, 2.00 mmol, 4.0 equiv.) at -20 or 0 . After stirring for 30 min, a solution of compound 1 or compound 4 (0.50 mmol, 1.0 equiv.) in THF (1 mL) was added. The resulting mixture was stirred before the completion of the reaction (monitored by TLC). Then the reaction mixture was poured into saturated NH4Cl solution (2.5 mL) at 0 and diluted with H2O (5 mL). The layers of the resulting mixture were separated and the aqueous layer was extracted with Et2O (4 × 15 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel to afford products.
  • 76
  • [ 4160-51-4 ]
  • [ 423115-90-6 ]
YieldReaction ConditionsOperation in experiment
With hydroxyamino hydrochloride; anhydrous Sodium acetate In ethanol at 60℃; for 6h; 88 First step, hydroxyamine hydrochloride (619 mg) and NaOAc (1.47 g) were added to a solution of 1-(4-methoxyphenyl)-butanone (800 mg) in EtOH (80 ml). The reaction mixture was stirred at 60°C for 6 h. EtOH was removed under reduced pressure. H2O (40 ml) was added to the residue, and the resulting solution was extracted with EtOAc (3 × 40 ml). The EtOAc of the combined organic layer was removed by rotary evaporation under reduced pressure to yield 1-(4-methoxyphenyl)-butanone oxime (870 mg) as a pale yellowish solid. Second step, a mixture of 1-(4-methoxyphenyl)-butanone oxime (870 mg) and concentrated HCl (2.38 ml) in EtOH (50 ml) was subjected to hydrogenation at atmospheric pressure in the presence of 10% Pd/C (90 mg). The reaction solution was filtered and the filtrate was concentrated. The residue was suspended in EtOAc, and the suspension was filtered to yield 1-(4-methoxyphenyl)-butylamine hydrochloride (965 mg) as a white solid. Third step, a mixture of 1-(4-methoxyphenyl)-butylamine (453 mg, the hydrochloride), 6-chloropurine riboside (200 mg) and triethylamine (3 ml) in PrOH (60ml) was heated to 70°C and reacted for 8 h. After evaporation of the reaction mixture, the residue was separated by column chromatography over silica gel and eluted with CHCl3-CH3OH (20 : 1) to yield N6-[(+/-)-1-(4-methoxyphenyl)-butyl]-adenosine(240 mg) as a white solid: positive ESIMS m/z 430 [M + H]+ and 352 [M + Na]+; 1H NMR (300 MHz, DMSO- d6): the adenosine moiety δ 8.37 (1H, s, H-2), 8.21 (1H, m, -NH), 8.17 (1H, brs, H-8), 5.89 (1H, d, J= 6.3 Hz, H-1'), 5.48 (2H, m, 2×-OH), 5.22 (1H, d, J= 4.8 Hz, -OH), 4.61 (1H, m, H-2'), 4.16 (1H, m, H-3'), 3.98 (1H, m, H-4'), 3.66 (1H, m, H-5'a), 3.56 (1H,, m, H-5'b); the (+/-)-1-(4-methoxyphenyl)-butyl moiety δ 7.36 (2H, d, J = 8.4 Hz, C-2", C-6"), 6.83 (2H, d, J = 8.4 Hz, C-3", C-5"), 5.32 (1H, m, H-7"), 3.76 (3H, s, -OH3), 1.91 (1H, m, H-8"a), 1.72 (1H, m, H-8"b), 1.24 (2H, m, H-9"), 0.86 (3H, t, J = 7.5 Hz, H-10"); 13C NMR (75 MHz, DMSO-d6): the adenosine moiety δ 154.3 (s, C-6), 152.4 (d, C-2), 148.5 (s, C-4), 140.0 (d, C-8), 119.8 (s, C-5), 88.2 (d, C-1'), 86.1 (d, C-4'), 73.6 (d, C-2'), 70.8 (d, C-3'), 61.8 (t, C-5'); the (+/-)-1-(4-methoxyphenyl)-butyl moiety δ 158.1 (s, C-4"), 136.3 (s, C-1"), 127.9 (d, C-2", C-6"), 113.7 (d, C-3", C-5"), 55.1 (q, -OCH3), 52.6 (d, C-7"), 38.2 (t, C-8"), 19.6 (t, C-9"), 13.7 (q, C-10").
870 mg With hydroxyamino hydrochloride; anhydrous Sodium acetate In ethanol at 60℃; for 6h; 88 First step, hydroxyamine hydrochloride (619 mg) and NaOAc (1.47 g) were added to a solution of 1-(4-methoxyphenyl)-butanone (800 mg) in EtOH (80 ml). The reaction mixture was stirred at 60° C. for 6 h.;EtOH was removed under reduced pressure. H2O (40 ml) was added to the residue, and the resulting solution was extracted with EtOAc (3*40 ml). The EtOAc of the combined organic layer was removed by rotary evaporation under reduced pressure to yield 1-(4-methoxyphenyl)-butanone oxime (870 mg) as a pale yellowish solid.
870 mg With hydroxyamino hydrochloride; anhydrous Sodium acetate In ethanol at 60℃; for 6h; 88.1 First step 1-(4-methoxyphenyl)-butanone (800 mg), hydroxylamine hydrochloride (619 mg) and anhydrous sodium acetate (1.47 g) were weighed and dissolved in ethanol (80 ml)And mixer reaction is carried out at 60 ° C for 6 h. The solvent was recovered with the reaction solution, suspended and dissolved with water (40 ml), extracted from ethyl acetate (40 ml '3), and the solvent was recovered with ethyl acetate layer to obtain a pale yellow solid 1-(4-methoxyphenyl)-butanone oxime (870 mg).
With hydroxyamino hydrochloride; anhydrous Sodium acetate In methanol at 20℃; Inert atmosphere;
With hydroxyamino hydrochloride; anhydrous Sodium acetate In ethanol 2.2 Typical procedure for preparation of ketoxime esters3 General procedure: To a mixture of hydroxylamine hydrochloride (278 mg, 4 mmol), NaOAc (640 mg, 8 mmol), EtOH (10 mL) was added aryl ketone A (2 mmol), and the mixture was stirred at 90 °C for 2 h or at r.t. overnight. The reaction mixture was cooled to room temperature, and then EtOH was removed under reduced pressure. The resulting mixture was extracted with EtOAc. The organic layer was then washed with brine and dried over Na2SO4. The solvent was removed under vacuum to give oxime B (> 99% yield) without further purification.

  • 77
  • [ 14367-86-3 ]
  • [ 4160-51-4 ]
YieldReaction ConditionsOperation in experiment
35% With magnesium(II) perchlorate; tris(2,2'-bipyridyl)ruthenium(II)chloride hexahydrate; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 12h; Inert atmosphere; Irradiation;
  • 78
  • [ 100-07-2 ]
  • [ 4160-51-4 ]
  • [ 71526-44-8 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1-(4-methoxyphenyl)-1-butanone With lithium hexamethyldisilazane In tetrahydrofuran; toluene at 0℃; for 0.00166667h; Inert atmosphere; Stage #2: 4-methoxy-benzoyl chloride In tetrahydrofuran; toluene for 0.0166667h; Inert atmosphere; Cooling with ice; 3.2.1. (3,5 Bis(4-methoxyphenyl)isoxazole) (5) General procedure: 4-Methoxyacetophenone (0.5 g, 3.3 mmol) was dissolved in 9mL of anhydrous toluene, cooled to 0 °C under argon and LiHMDS (3.5 mL, 1.0 M in THF, 3.5 mmol) and added via a syringe in one-pot under stirring. After approximately 1 min to allow the formation of the anion, p-anisoyl chloride (0.23 mL, 1.65 mmol) was added. Theice bath was removed and after 1 min 4 mL of AcOH was added. The reaction was stirred for an additional 2 min and consecutively EtOH (17 mL), THF (4 mL) and an excess of hydrochloric hydroxylamine (1.03 g, 15 mmol) were added. The reaction mixture was refluxed for 15 min and completion of the reaction was verified by TLC. Then, the resulting solution was added to 5 mL of 1.0 M NaOH and extracted twice with EtOAc (2 x 20 mL). The combined organic fractions were washed with brine, dried over Na2SO4, and evaporated under reduced pressure. The resulting residue was purified byflash column chromatography using a mixture of CH2Cl2/n-hexane(9:1) to provide isoxazole 6 (0.75 g, 80%) as white crystalline needles.
  • 79
  • [ 164171-80-6 ]
  • [ 4160-51-4 ]
YieldReaction ConditionsOperation in experiment
97% With 2,4,6-trimethyl-pyridine; iron(III) chloride; 1,2-bis(2,4,6-triisopropylphenyl)disulfane; tetrabutyl-ammonium chloride In 1,2-dichloro-ethane for 24h; Schlenk technique; Inert atmosphere; Irradiation; Sealed tube;
71% With 2,3,5-trimethyl-pyridine; [Ir(2-(2,4-difluorophenyl)-5-(trifluoromethyl)pyridine)2(5,5'-bis(trifluoromethyl)-2,2'-bipyridyl)](PF6); thiophenol In dichloromethane at 20℃; Sealed tube; Inert atmosphere; Irradiation;
  • 80
  • [ 34813-49-5 ]
  • [ 4160-51-4 ]
  • (E)-N-(1-(4-methoxyphenyl)butylidene)-2-methylpropane-2-sulfonamide [ No CAS ]
  • 81
  • [ 64-17-5 ]
  • [ 100-06-1 ]
  • [ 4160-51-4 ]
YieldReaction ConditionsOperation in experiment
74% With trifuran-2-yl-phosphane; C48H34F6N4O4Pd2; lithium hydroxide In neat (no solvent) at 100℃; for 24h; Inert atmosphere; Schlenk technique; Sealed tube;
  • 82
  • [ 45842-10-2 ]
  • [ 164171-80-6 ]
  • 1-(4-methoxyphenyl)-4-((2,2,6,6-tetramethylpiperidin-1-yl)oxy)-butan-1-one [ No CAS ]
  • [ 4160-51-4 ]
  • [ 1078-19-9 ]
YieldReaction ConditionsOperation in experiment
1: 54% 2: 16% 3: 7 mg With sodium persulfate; silver nitrate In water; dimethyl sulfoxide at 50℃; for 16h; Inert atmosphere;
  • 83
  • [ 2537-48-6 ]
  • [ 4160-51-4 ]
  • (E)-3-(4-methoxyphenyl)hex-2-enenitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% Stage #1: diethyl 1-cyanomethylphosphonate With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 1h; Stage #2: 1-(4-methoxyphenyl)-1-butanone In tetrahydrofuran; mineral oil at 0 - 20℃; for 25h;
  • 84
  • [ 123-73-9 ]
  • [ 5720-07-0 ]
  • [ 4160-51-4 ]
YieldReaction ConditionsOperation in experiment
57% With rhodium(II) acetate dimer; water; potassium carbonate; tri tert-butylphosphoniumtetrafluoroborate In toluene at 90℃; for 6h; Inert atmosphere; Sealed tube;
  • 85
  • [ 64-18-6 ]
  • [ 696-62-8 ]
  • [ 106-94-5 ]
  • [ 4160-51-4 ]
YieldReaction ConditionsOperation in experiment
75% With tris-(dibenzylideneacetone)dipalladium(0); acetic anhydride; magnesium; triphenylphosphine; zinc(II) chloride In tetrahydrofuran at 55℃; for 12h; Inert atmosphere; Sealed tube;
  • 86
  • [ 504-29-0 ]
  • [ 4160-51-4 ]
  • [ 14547-81-0 ]
YieldReaction ConditionsOperation in experiment
33% With tert.-butylhydroperoxide; trifluorormethanesulfonic acid; tetra-(n-butyl)ammonium iodide In water at 80℃; Sealed tube;
  • 87
  • [ 4160-51-4 ]
  • 1-methoxy-4-(2-methylhexan-3-yl)benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium <i>tert</i>-butylate / dimethyl sulfoxide / Schlenk technique; Inert atmosphere; Reflux 2: hydrogen; C23H43IrN2OP(1+)*C32H12BF24(1-) / dichloromethane / 36 h / 23 °C / 1500.15 Torr / Autoclave
  • 88
  • [ 24470-78-8 ]
  • [ 4160-51-4 ]
  • 1-methoxy-4-(2-methylhex-2-en-3-yl)benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
25% With potassium <i>tert</i>-butylate In dimethyl sulfoxide Schlenk technique; Inert atmosphere; Reflux;
  • 89
  • [ 1779-49-3 ]
  • [ 4160-51-4 ]
  • 1-methoxy-4-(pent-1-en-2-yl)benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% Stage #1: Methyltriphenylphosphonium bromide With sodium hydride In tetrahydrofuran; mineral oil at 0℃; Stage #2: 1-(4-methoxyphenyl)-1-butanone In tetrahydrofuran; mineral oil at 0℃; Reflux;
82% Stage #1: Methyltriphenylphosphonium bromide With potassium <i>tert</i>-butylate In tetrahydrofuran at 0℃; for 0.75h; Stage #2: 1-(4-methoxyphenyl)-1-butanone In tetrahydrofuran at 20℃; for 16h;
  • 90
  • [ 33513-42-7 ]
  • [ 4160-51-4 ]
  • [ 100117-47-3 ]
YieldReaction ConditionsOperation in experiment
50% With <i>N</i>,<i>N</i>-dimethyl-formamide dimethyl acetal at 120℃; for 72h; 1 Step 1. 2-(4-Methoxybenzoyl)butanal. A mixture of 319 1-(4-methoxyphenyl)butan-1-one (5.0 g, 28 mmol) and 320 DMF-DMA (7.4 mL, 56 mmol) in 12 DMF (56 mL) was stirred at 120° C. for 72 h, then cooled, diluted with ether, washed with water, brine, dried (MgSO4) and evaporated. The residue was purified (FCC, SiO2, 10-30% EtOAc/heptanes) to provide the 321 title compound (2.90 g, 50%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 9.71 (d, J=3.30 Hz, 1H), 7.98 (d, J=9.05 Hz, 2H), 6.99 (d, J=8.93 Hz, 2H), 4.21 (dt, J=3.30, 6.91 Hz, 1H), 3.91 (s, 3H), 1.96-2.23 (m, 2H), 1.00 (t, J=7.46 Hz, 3H). [M+H]=206.9.
  • 91
  • 2-((difluoromethyl)sulfinyl)pyridine [ No CAS ]
  • [ 4160-51-4 ]
  • C12H14F2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide at -65 - -55℃; for 3h; Inert atmosphere;
  • 92
  • [ 5720-07-0 ]
  • [ 4160-51-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: palladium diacetate; 1,3-bis-(diphenylphosphino)propane / acetone / 15 h / 70 °C 2: hydrogenchloride / acetone / 1 h / 20 °C
  • 93
  • [ 4160-51-4 ]
  • (1S,2R)-2-fluoro-1-(4-methoxyphenyl)butan-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: n-butyllithium; diisopropylamine / hexane; tetrahydrofuran / 1.5 h / -78 °C 1.2: 12 h / -78 - 20 °C 2.1: bis(1,5-cyclooctadiene)diiridium(I) dichloride; sodium hydroxide; hydrogen / isopropyl alcohol / 12 h / 25 °C / 750.08 Torr / Autoclave
  • 94
  • [ 4160-51-4 ]
  • 2-fluoro-1-(4-methoxyphenyl)butan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% Stage #1: 1-(4-methoxyphenyl)-1-butanone With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 1.5h; Stage #2: With N-fluorobis(benzenesulfon)imide In tetrahydrofuran; hexane at -78 - 20℃; for 12h;
  • 95
  • [ 4160-51-4 ]
  • C18H18FNO5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: n-butyllithium; diisopropylamine / hexane; tetrahydrofuran / 1.5 h / -78 °C 1.2: 12 h / -78 - 20 °C 2.1: bis(1,5-cyclooctadiene)diiridium(I) dichloride; sodium hydroxide; hydrogen / isopropyl alcohol / 12 h / 25 °C / 750.08 Torr / Autoclave 3.1: triethylamine / dichloromethane / 0 - 20 °C
  • 96
  • [ 109480-78-6 ]
  • [ 13139-86-1 ]
  • [ 4160-51-4 ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran at 0 - 50℃; for 1h;
  • 97
  • [ 73183-34-3 ]
  • [ 4160-51-4 ]
  • CH3OC6H4C(CHCH2CH3)B(O2C2(CH3)4) [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% Stage #1: 1-(4-methoxyphenyl)-1-butanone With magnesium methanolate; lithium diisopropyl amide In 1,2-dimethoxyethane at -30℃; for 0.0833333h; Inert atmosphere; Sealed tube; Stage #2: bis(pinacol)diborane In 1,2-dimethoxyethane at 25℃; for 12h; Inert atmosphere; 2 Under a nitrogen atmosphere, the 4-methoxyphenylbutanone (0.5mmol, 1.0 equiv., 89.1mg), magnesium methoxide (1.0 equiv., 43.2 mg), ethylene glycol dimethyl ether (1.5 mL) and magnets were added to the baked 25 mL glass pressure tube. Then cool the glass pressure tube to -30, add lithium diisopropylamide (1.1equiv.), stir for 5 minutes. After the stirring was completed, diboronic acid pinacol borate (1.2 equiv., 152.4 mg) was added at room temperature, and the temperature was raised to 25° C. and stirred for 12 hours. After the reaction, ethyl acetate was added to the system for extraction, the product was separated by column chromatography with a yield of 85%, Z:E>20:1.
  • 98
  • [ 75-77-4 ]
  • [ 4160-51-4 ]
  • (Z)-(1-(4-methoxyphenyl)but-1-enyloxy)trimethylsilane [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% Stage #1: 1-(4-methoxyphenyl)-1-butanone With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: chloro-trimethyl-silane In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere; stereoselective reaction;
  • 99
  • [ 4160-51-4 ]
  • (E)-1-(4-methoxyphenyl)-N-(phenylethynyl)butan-1-imine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: hydroxylamine hydrochloride; sodium acetate / methanol / 20 °C / Inert atmosphere 2: triethylamine / dichloromethane / 5 h / 0 - 20 °C / Inert atmosphere 3: copper diacetate; 2,2'-biquinoline; potassium carbonate / 1,2-dichloro-ethane / 48 h / 110 °C / Sealed tube; Inert atmosphere
  • 100
  • [ 4160-51-4 ]
  • 1-(4-methoxyphenyl)butan-1-one O-acetyl oxime [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: hydroxylamine hydrochloride; sodium acetate / methanol / 20 °C / Inert atmosphere 2: triethylamine / dichloromethane / 5 h / 0 - 20 °C / Inert atmosphere
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