HCID 22461690, compound → Ethyl 4-(3-cyano-4-hydroxyphenyl)butanoate

Participants

Reaction Steps

To a solution of ethyl 4-(3-bromo-4-hydroxyphenyl)butanoate (19.8 g, 69 mmol) in 172 mL of N-methyl-2-pyrrolidinone was added CuCN (6.49 g, 72.4 mmol). The solution was heated to reflux for 4 hours then cooled to room temperature. The reaction was diluted with EtOAc and washed twice with 5% HCl and once with brine, then dried over sodium sulfate and concentrated. Purified on silica gel using 60:40 hexanes:EtOAc as the elutant. The yield of ethyl 4-(3-cyano-4-hydroxyphenyl)butanoate was 9.84 g (61%): 1H-NMR (CDCl3) 7.67 (1H, s), 7.24-7.29 (2H), 7.94 (1H, d), 4.14 (2H, q), 2.59 (2H, dd), 2.34 (2H, dd), 1.91 (2H, m), 1.28 (3H, t).

Provenance & Evidence