[Li+].[BH4-].[Cl:3][C:4]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[C:11]([O:17][CH3:18])=[CH:10][C:5]=1[C:6](OC)=[O:7].CCOC(C)=O.[NH4+].[Cl-]>C1COCC1>[Cl:3][C:4]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[C:11]([O:17][CH3:18])=[CH:10][C:5]=1[CH2:6][OH:7]
A 2M solution of LiBH4 in THF (2 mmol) was added drop-wise to a stirred solution of methyl 2-chloro-5-methoxy-4-nitrobenzoate (1 mmol) in dry THF (10 mL) at 0° C. The mixture was allowed to warm to room temperature and stirred for 5 hours. EtOAc (10 mL) was added to the mixture followed by saturated NH4Cl solution (2 mL) and stirring continued for 15 minutes. The mixture was partitioned between EtOAc (10 mL) and water (10 mL) and the separated aqueous phase was extracted with EtOAc (10 mL). The combined organic extracts were dried (Na2SO4) and concentrated under reduced pressure to afford the title compound (89%) which was used without further purification.
Loading…
