Sodium borohydride → 4-(4-Bromophenoxy)cyclohexanol
Reaction equation
[BH4-].[Na+].[Br:3][C:4]1[CH:17]=[CH:16][C:7]([O:8][CH:9]2[CH2:14][CH2:13][C:12](=[O:15])[CH2:11][CH2:10]2)=[CH:6][CH:5]=1>C(O)C>[Br:3][C:4]1[CH:5]=[CH:6][C:7]([O:8][CH:9]2[CH2:10][CH2:11][CH:12]([OH:15])[CH2:13][CH2:14]2)=[CH:16][CH:17]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Sodium borohydride (77.3 mg, 2.04 mmol) was added to a solution of 4-(4-bromophenoxy)cyclohexanone (500 mg, 1.86 mmol) in ethanol (10 mL) at room temperature. After 20 minutes the reaction was cooled to 00° C. and quenched by the addition of 1 N HCl (aq). The reaction was concentrated and the resulting residue was partitioned between ether and 1 N HCl (aq). The layers were separated, the organic layer was washed with water then dried (Na2SO4), filtered and concentrated. Purification on an Analogix SF15-12 g column (hexanes/ethyl acetate=8:2) afforded the title compound as a white solid (360 mg, 72%).