Water → HCID 19597961, compound

Participants

Reaction Conditions

Reaction Steps

A solution of lithium diisopropylamide in cyclohexane (5.13 mmol, 3.42 ml of a 1.5M solution) was added dropwise to a solution of (2-chlorobenzo[b]thiophen-3-yl)acetonitrile (1.06 g, 5.13 mmol) in tetrahydrofuran (10 ml) cooled to -70° C. under nitrogen. The resulting solution was stirred at -70° C. for 20 min, then a solution of 5-iodo-1,1-difluoropentane (1.2 g, 5.13 mmol) in tetrahydrofuran (5 ml) was slowly added at -70° C. The reaction mixture was stirred at -70° C. for 1 hr, then slowly allowed to warm to room temperature and left at that temperature overnight. Water (60 ml) was added to the reaction solution and the resulting mixture was extracted with ethyl acetate (3×70 ml). The combined ethyl acetate extracts were washed with brine (80 ml), dried (sodium sulfate) and concentrated in vacuo. The crude product (2.1 g) was purified by column chromatography on silica gel (200 g), eluting with 4:1 hexane/dichloromethane followed by 7:3 hexane/dichloromethane to yield the title compound as an oil (950 mg, 59% yield). 1H NMR (300 MHz, CDCl3) δ1.4-1.7 (c, 4H), 1.7-2.05 (c, 3H), 2.2 (c, 1H) 4.3 (t, 1H), 5.6, 5.78, 5.98 (3t, total 1H), 7.42 (m, 2H), 7.75 (d, 1H), 7.95 (d, 1H).

Provenance & Evidence