Acetic Anhydride → HCID 13197843, compound

Participants

Reaction Conditions

Reaction Steps

A 250 mg (1.4 mmol) quantity of 6-hydroxy-7-methoxytetralin was dissolved in 1 mL of dry THF. To the solution of 6-hydroxy-7-methoxytetralin was added 4-dimethylaminopyridine (DMAP, 476 mg, 4.2 mmol) in 6 ml of dry THF and acetic anhydride 446 mg (4.37 mmol) in 1.5 mL, of dry THF. The reaction solution was stirred under a dry atmosphere at 25° C. for 18 hours, after which time the solvent was evaporated to dryness. The resulting residue was dissolved in EtOAc (40 mL) and the EtOAc layer washed with water (2×5 mL), 5% NaHCO3 (aq) (2×5 mL), 1 M HCl (5×5 mL), water (5 mL), and brine (2×5 mL). The organic layer was dried over MgSO4 and evaporated to dryness. The residue was purified by flash chromotography (hexane : EtOAc, 4:1) to give 290 mg (94% yield) of 6-acetoxy-7-methoxytetralin. IR 3003, 2930, 2860, 2840, 1767 (C═O str.), 1619, 1512, 1266, 1219, 1195, 1104, 1026; 1H NMR (CDCl13) δ6.73 (1H, s), 6.66 (1H, s), 3.79 (3H, s, —OCH3), 2.68-2.74 (4H, m), 2.30 (3H, s, —OCOCH3), 1.78 (4H, qn, J=3.25 Hz); 13C NMR (CDCl3) δ6.73 169.3, 148.6, 137.5, 135.3, 129.3, 122.8, 112.8, 55.8, 29.3, 28.4, 23.0, 20.5; LRMS EI m/z 220[M+], 178 [M+, base peak].

Provenance & Evidence