Oxalyl chloride → 5-(Benzyloxy)pentanoyl chloride

Participants

Reaction Steps

To a solution of the acid 29 (4.98 g, 24 mmol) in dry benzene (40 ml), was added oxalyl chloride (2.5 ml, 28.8 mmol, 1.2 equiv) dropwise. A drying tube was placed on the flask and the reaction was stirred for 90 min at room temperature. The reaction was concentrated in vacuo and used directly in the next step: 1H NMR (400 MHz, CDCl3) δ 7.38-7.27 (m, 5H), 4.50 (s, 2H), 3.51-3.40 (t, 3J=6.4 Hz, 2H), 2.95-2.90 (t, 3J=7.2 Hz, 3H), 1.87-1.78 (m, 2H), 1.71-1.63 (m, 2H); 13C NMR (75 MHz, CDCl3) δ 173.958, 138.519, 128.949, 128.787, 128.630, 127.862, 73.197, 69.551, 47.032, 28.618, 22.329.

Provenance & Evidence