Thionyl Chloride → HCID 23295002, compound

Participants

Reaction Conditions

Reaction Steps

1-Phenylcyclobutanecarboxylic acid (1.9 mmol) was refluxed with SOCl2 (5 mL). After 0.5 h, the reaction mixture was evaporated and the residue dissolved in toluene. Diisopropylaminoethanol (3.8 mmol) was added and the mixture was heated at 80° C. for 1.5 h. The reaction mixture was filtered and chromatographed on silica gel using toluene-Et3N 95:5 as eluent. The yield was 1.3 g (73%); mp 137-139° C.; 1H NMR (D2O) δ 1.25 (t, 6H), 1.92-2.01 (m, 1H), 2.07-2.16 (m, 1H), 2.64 (m, 2H), 2.89 (m, 2H), 3.11 (q, 4H), 3.50 (t, 2H), 4.48 (t, 2H), 7.44 (m, 1H), 7.48 (m, 2H), 7.53 (m, 2H). Anal. (C17H25NO2.HCl) C, H, N.

Provenance & Evidence