Dimethylformamide → 2-Thiophenemethanol, 4-(trifluoromethyl)-

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Reaction Conditions

Reaction Steps

To a solution of 2,2,6,6-tetramethylpiperidine (7.79 g) in THF (150 ml) was added n-butyllithium (1.6 M in hexane, 34.5 ml) at −78° C., and the mixture was stirred at 0° C. for 10 min. The solution was cooled to −78° C., and stirred for 30 min. To the solution was added 3-(trifluoromethyl)thiophene (6.99 g) in THF over 30 min, and the mixture was stirred for 1 h at same temperature. Then DMF (10.1 g) was added to the mixture, and the mixture was stirred overnight at room temperature. The mixture was quenched with 1 M HCl and extracted with EtOAc. The organic layer was separated, washed with 1 M HCl and brine successively, dried over MgSO4, concentrated in vacuo, and purified by column chromatography (hexane/EtOAc). The resulting residue was dissolved in MeOH (100 ml), and NaBH4 (0.865 g) was added to the mixture at 0° C. After stirred at room temperature for 30 min, the mixture was quenched with saturated NH4Cl solution and extracted with EtOAc. The organic layer was separated, washed with saturated NH4Cl solution and brine successively, dried over MgSO4 and concentrated in vacuo. The residue was purified by column chromatography (hexane/EtOAc) to give the title compound (1.79 g) as a colorless oil.

Provenance & Evidence