HCID 10503817, compound → HCID 54335570, compound

Participants

Reaction Steps

A stirred suspension of methyltriphenylphosphonium bromide (2.4 g) in tetrahydrofuran (50 mL) at ambient temperature is treated with a solution of butyllithium in hexanes (2.6 mL; 2.5 M). After two hours, the reaction mixture is treated with a solution of ethyl (RS)-4-[2-acetyl-5-(3-thienylmethoxy)phenoxy]-4-(2-methylphenyl)-butanoate (1 g) in tetrahydrofuran (2 mL) and stirred for a further two hours. It is then partitioned between hydrochloric acid (50 mL; 1 N) and ethyl acetate (100 mL). The organic layer is washed with water (50 mL), dried over magnesium sulphate, filtered and concentrated in vacuo. The residue is subjected to flash chromatography on silica gel, eluting with a mixture of ethyl acetate and cyclohexane (1:9 v/v) to give ethyl (RS)-4-(2-methylphenyl)-4-[2-(propen-2-yl)-5-(3-thienylmethoxy)phenoxyl]butanoate (0.7 g), in the form of a colourless oil.

Provenance & Evidence