Sodium bis(trimethylsilyl)amide → 4-(2,3-Dihydro-1-benzofuran-7-yl)but-3-enoic acid

Participants

Reaction Steps

To a solution of (2-carboxyethyl)triphenylphosphonium bromide (617 mg, 1.5 mmol) in THF (20 mL) was added NaHMDS (1.5 mL, 3.0 mmol) at −20° C., and the reaction was stirred for 20 min. 2,3-Dihydro-1-benzofuran-7-carbaldehyde (200 mg, 1.4 mmol) was added to the reaction at −78° C., and the reaction was stirred overnight while warming to rt. The reaction was diluted with water (30 mL) and extracted with EtOAc (3×30 mL). Organics were washed with brine (30 mL), dried (Na2SO4), and concentrated to give the crude title compound as a yellow solid. [M+H] Calc'd for C12H12O3, 205. Found, 205.

Provenance & Evidence