Dimethylformamide → HCID 57989086, compound

Participants

Reaction Steps

tert-Butyl(3-(2-fluorophenyl)propoxy)dimethylsilane [Aromatic Intermediate 24, step b] (4.4 g) was added dropwise over 5 min to a solution of sec-butyllithium (1.4M in cyclohexane, 11.7 mL) and 1,1,4,7,7-pentamethyldiethylenetriamine (3.4 mL) in THF (25 mL) at −78° C. The resulting mixture was stirred for 2 h, then DMF (6.4 mL) was cautiously added and the resulting mixture allowed to warm to RT and stirred overnight. The reaction was quenched with water (100 mL) and then ethyl acetate (250 mL) was added. The phases were separated and the organic phase washed with water (2×100 mL), aqueous HCl (2M, 2×50 mL), and brine (100 mL), then dried over magnesium sulphate, filtered and evaporated. Purification was by silica gel chromatography eluting with isohexane to 10% ether in isohexane gradient. The fractions containing product were combined and evaporated to give the titled compound as a clear oil. Yield 1.0 g.

Provenance & Evidence