HCID 11299024, compound → 2-Methyl-2-(4-nitrophenyl)propan-1-ol
Reaction equation
[CH3:1][C:2]([C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)([CH3:7])[C:3](OC)=[O:4]>C1COCC1>[CH3:7][C:2]([C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)([CH3:1])[CH2:3][OH:4]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of methyl 2-methyl-2-(4-nitrophenyl)propionate (5.32 g, 23.8 mmol, Step A) in THF (200 mL) at 0° C. was added a solution of BH3 1M in THF (25.8 mL, 45.8 mmol). The reaction was stirred at RT overnight and quenched with MeOH. THF was evaporated under reduced pressure and the residue was diluted in EtOAc and aqueous 1M HCl was added. The mixture was extracted with EtOAc, the organic layer was dried over MgSO4 and evaporated under reduced pressure. The product was purified by flash chromatography using 40% EtOAc-hexane to give the title compound as a yellow solid.