Acetyl chloride → HCID 86743523, compound

Participants

Reaction Steps

A solution of the diester (26A) (42 mg, 0.095 mmol) and acetyl chloride (0.1 ml, 0.11 g, 1.41 mmol) in dry dichloromethane (1 ml) was treated with anhydrous aluminium chloride (63 mg, 0.47 mmol) at room temperature. After being stirred to 30 min, a saturated aqueous solution of sodium bicarbonate was added, and the mixture was extracted with dichloromethane and worked up in the usual manner to give an oil which was chromatographed on silica (2 g). Elution with ether-light petroleum (1:5) gave the product (27) (43 mg, 93%), as an oil, νmax 1730 and 1685 cm-1 (C=O), δ (250 MHz) 7.75 (1 H, dd, J 8 and 1.5 Hz, 3-proton), 7.64 (1 H, d, J 1.5 Hz, 1-proton), 7.20 (1 H, d, J 8 Hz, 4-proton), 5.52 (1 H, dt, J 10.5 and 5.5 Hz, 11-proton), 4.66 (1 H, dd, J 9 and 7 Hz, 17-proton), 2.89 (2 H, t, J 7 Hz, 6-protons), 2.53 (3 H, s, CH3CO), 2.37-1.25 (11 H, m), 1.23 (18 H, two s, OBut), 0.89 (3 H, s, 18-CH3), M+ (ammonia chemical iionization) 500 (M+NH3).

Provenance & Evidence