Sodium hydride → HCID 54574257, compound

Participants

Reaction Steps

2-Hydroxy-4-(3-thienylmethoxy)benzonitrile (2.5 g) is added portionwise to a stirred suspension of sodium hydride (0.44 g, 60% dispersion in mineral oil) in dry dimethyl formamide (30 mL). After stirring at ambient temperature for 30 minutes, ethyl (RS)-4-chloro-4-(2-cyanophenyl)butanoate (2.87 g) is added in one portion and the reaction stirred for 16 hours at 100° C. The reaction is concentrated in vacuo and the residue partitioned between ethyl acetate (100 mL) and water (100 mL). The organic phase is dried over magnesium sulphate, filtered and concentrated in vacuo. The residual oil is purified by flash chromatography on silica eluting with a mixture of ethyl acetate and pentane (1:2 v/v). Fractions homogeneous in the required product are combined and evaporated to give ethyl (RS)-4-(2-cyanophenyl)-4-[2-cyano-5-(3-thienylmethoxy)phenoxy]butanoate (250 mg) as an orange oil.

Provenance & Evidence