Water → HCID 23130519, compound

Participants

Reaction Steps

n-Butyl lithium (2.44N hexane solution, 6.4 mL, 16.9 mmol) was added dropwise to a solution of 2-(5-bromo-thiophen-2-yl)-[1,3]dioxolane (3.0 g, 13 mmol) in tetrahydrofuran (30 mL) at from −75° C. to −69° C., and the solution was stirred for 17 minutes. 3-Fluorobenzyl bromide (1.7 mL, 14.3 mmol) was added dropwise to this reaction solution at from −75° C. to −69° C. After dropwise addition was completed, the reaction solution was gradually allowed to room temperature. Water and ethyl acetate were added to the reaction solution, which was then partitioned, the organic layer was concentrated in vacuo, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1), and the title compound (478 mg, 1.81 mmol, 13.9%) was obtained as a brown oil.

Provenance & Evidence