Oxalyl chloride → (S)-2-(4-fluorophenyl)pent-4-enoyl chloride

Participants

Reaction Steps

(2S)-2-(4-Fluorophenyl)pent-4-enoic acid (see Tetrahedron Letters; 2002; 6617-6620; 1.2 g, 6.0 mmol) was dissolved in CH2Cl2 (15 mL) and to the resultant solution was added oxalyl chloride (1.1 g, 9.0 mmol) followed by one drop of DMF. The mixture was stirred for 2 h at room temperature. The solvent was removed by evaporation and there was obtained 1.2 g (98%) of (2S)-2-(4-fluorophenyl)pent-4-enoyl chloride as an oil. 1H NMR (300 MHz, CDCl3): 2.6 (q, 1H), 2.9 (q, 1H), 4.1 (t, 1H), 5.0-5.2 (m, 2H), 5.6-5.8 (m, 1H), 7.1 (t, 2H), 7.3 (m, 2H).

Provenance & Evidence