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
Conditions
- Temperature
- 0 °C
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 0° C. and quenched by the addition of 1N HCl (aq). The reaction was concentrated and the resulting residue was partitioned between ether and 1N HCl (aq). The layers were separated, the organic layer was washed with water then dried (Na2SO4), filtered and concentrated. Purification on an Analogix SF15-12g column (hexanes/ethyl acetate=8:2) afforded the title compound as a white solid (360 mg, 72%).