Ammonium Chloride → HCID 69432581, compound

Participants

Reaction Steps

Under a nitrogen atmosphere, sodium borohydride (343 mg, 9.07 mmol) was added to a solution of 3-(1-methyl-1-nitroethyl)cyclohexanone (1.68 g, 9.07 mmol) known in literature in methanol (17 ml) at 0° C. After 45 minutes, a saturated aqueous ammonium chloride solution was added to the reaction solution and then the methanol was concentrated under reduced pressure. The resulting aqueous solution was diluted with water and extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate. The organic layer dried was concentrated under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate) to obtain cis-3-(1-methyl-1-nitroethyl)cyclohexanol (499.1 mg, 29%), trans-3-(1-methyl-1-nitroethyl)cyclohexanol (259.6 mg, 15%) and a mixture of the isomers (55%).

Provenance & Evidence