Acetic Anhydride → HCID 68817532, compound

Participants

Reaction Steps

A mixture of (2R)-2-[(5-methoxy-2-nitrophenoxy)methyl]oxirane (620 mg, 2.75 mmol), Pd/C (10%, 250 mg), N-ethyl-N-isopropylpropan-2-amine (0.94 mL, 5.5 mmol) and acetic anhydride (0.52 mL, 5.5 mmol) in ethyl acetate (25 mL) was hydrogenated at atmospheric pressure at room temperature for 40 minutes. The catalyst was filtered off and the filtrate was concentrated in vacuo. The residue was purified by silica gel flash chromatography (0-60% ethyl acetate in petroleum spirit) to give sub-title compound (155 mg) and 204 mg of N-[2-(2-hydroxypropoxy)-4-methoxyphenyl]acetamide (see example 14). 1H-NMR (CDCl3, 400 MHz): δ 8.22 (d, J=8.8 Hz, 1H); 7.64 (br.s, 1H); 6.55-6.49 (m, 2H); 4.34 (dd, J=2.5, 11.3 Hz, 1H); 3.94 (dd, J=6.1, 11.3 Hz, 1H); 3.78 (s, 3H); 3.39 (m, 1H); 2.96 (t, J=4.5 Hz, 1H); 2.78 (dd; J=2.6, 4.8 Hz, 1H); 2.20 (s, 3H).

Provenance & Evidence