Dimethylformamide → 2-Methylpentane

Participants

Reaction Conditions

Reaction Steps

2,2,6,6-Tetramethylpiperidine (3.0 g) was added dropwise to a stirred solution of n-butyllithium (1.6M in hexanes, 13 mL) in dry tetrahydrofuran (12 mL) at −78° C. After 10 min, 2-(4-fluorophenyl)ethanol (1.00 g) was added dropwise. The reaction mixture was stirred at −78° C. for 5 h and then dry DMF (3.18 mL) was added dropwise over 5 min. The cooling bath was removed and the reaction mixture allowed to warm to room temperature overnight. Ethyl acetate and aqueous HCl (2M) were added and the solution separated. The ethyl acetate layer was washed with water, brine, dried over sodium sulphate, filtered and evaporated in vacuo. Purification was by silica gel chromatography eluting with ethyl acetate:isohexane, 1:1 to give the subtitled compound as an oil. Yield 0.43 g.

Provenance & Evidence