Water → HCID 25140028, compound

Participants

Reaction Conditions

Reaction Steps

Ac2O (47 mL, 505 mmol) in DCM (50 mL) was added over 1 h to a stirred solution of alcohol 149 (54.5 g, 337 mmol), pyridine (52 mL, 981 mmol) and DMAP (1.65 g, 13 mol) in DCM (400 mL) and the resulting solution was stirred at 20° C. for 16 h. H2O (200 mL) was added, and the mixture stirred for 1 h. The organic fraction was washed with aqueous HCl solution (1 M, 100 mL) and H2O (150 mL), dried and the solvent evaporated to give acetate 150 (68.4 g, 99%) as a pale brown oil: 1H NMR δ 7.16-7.19 (m, 2H, Harom), 7.09-7.14 (m, 2H, Harom), 4.16 (t, J=6.8 Hz, 2H, CH2O), 3.04-3.10 (m, 2H, CH2), 2.48-2.66 (m, 3H, CH2, CH), 2.05 (s, 3H, COCH3), 1.85 (q, J=6.8 Hz, 2H, CH2); 13C NMR δ 171.1, 143.0 (2), 126.2 (2), 124.4 (2), 63.5, 39.1 (2), 37.0, 34.3, 21.0. Anal calcd for C13H16O2: C, 76.4; H, 7.9. Found: C, 76.6; H, 7.9%.

Provenance & Evidence