Ethanol → 2-(3-Methoxy-phenyl)-2-propyl-cyclohexanone

HRID 2076044Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C:10]2=[O:15])[CH:6]=[CH:7][CH:8]=1.[H-].[Na+].I[CH2:19][CH2:20][CH3:21].C(O)C>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2([CH2:19][CH2:20][CH3:21])[CH2:14][CH2:13][CH2:12][CH2:11][C:10]2=[O:15])[CH:6]=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 22.5 °C

Procedure

A solution of 2-(3-methoxy-phenyl)-cyclohexanone (2.04 g, 10.0 mmol) in N,N-dimethylformamide (10 mL) was added over 10 min to a mixture of sodium hydride (0.29 g, 12.0 mmol) in N,N-dimethylformamide (4 mL), the temperature being kept below 30° C. The reaction mixture was stirred at 20-25° C. for 2 h. A solution of 1-iodo-propane (1.17 mL, 12.0 mmol) in N,N-dimethylformamide (2 mL) was added over 10 min at 20-25° C. The mixture was stirred for 18 h, and then, ethanol (2 mL) was slowly added. The mixture was stirred for 0.5 h and then poured onto ice-water. The mixture was extracted with dichloromethane. The organic layer was separated, washed with water, and dried over sodium sulfate. Solvents were removed under reduced pressure and the remaining oil was purified by column chromatography on silica gel using heptane/diethyl ether (4:1, v/v) as eluent to give the title compound (0.74 g, ca. 30%) as pale-yellow oil. MS ISP (m/e): 247.3 [(M+H)+].

Workup

custombeing kept below 30° C
stirringThe mixture was stirred for 18 h
stirringThe mixture was stirred for 0.5 h
additionpoured onto ice-water
extractionThe mixture was extracted with dichloromethane
customThe organic layer was separated
washwashed with water
dry with materialdried over sodium sulfate
customSolvents were removed under reduced pressure
customthe remaining oil was purified by column chromatography on silica gel

Sources & evidence

ORD record: ord-f90ab1961a7d4c7e996e43b9c0779903
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07923450B2

Reaction notes

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