Cyclohexyl phenyl ketone → HCID 86680291, compound

Participants

Reaction Steps

Cyclohexyl phenyl ketone (5.0 g, 27 mmol) was dissolved in ethanol (50 mL) and cooled by ice. Sodium borohydride (510 mg, 13.5 mmol) was added thereto at 0° C. The completion of the addition, the mixture was heated to a room temperature, and the disappearance of the raw material was confirmed by TLC. The reaction solution was concentrated and then diluted with water, and the diluted solution was neutralized with a 1-N hydrochloric acid aqueous solution. Ethyl acetate was added thereto, the mixture was subjected to extraction. Then the extract was dried over sodium sulfate. The solvent was distilled off, and the residue was used for the next step without purification. The resulting viscous oil was dissolved in dichloromethane (10 mL), and thionyl chloride (10 mL, 140 mmol) was added dropwise thereto at a room temperature. After the dropping was completed, the completion of the reaction was confirmed by TLC. After the completion of the reaction, toluene was added to the reaction mixture, and unreacted thionyl chloride was distilled off. The resulting light-yellow oil and 1-carboethoxy-4-hydroxypiperidine (2.1 g, 12 mmol) were mixed, and the mixture was stirred at an oil bath temperature of 130° C. overnight. After the completion of the reaction was confirmed by TLC, the reaction mixture was allowed to cool down. Ethyl acetate was added to the resulting residue, and then the resulting mixture was washed with water. The organic layer was dried over sodium sulfate, and then the solvent was distilled off. Thus a brown oil was obtained. The resulting oil was purified by silica gel column chromatography (hexane/ethyl acetate (volume ratio)=10:1) to give the title compound (5.1 g, 510).

Provenance & Evidence