Dichloromethane → Dichloromethane methanol ammonium hydroxide

Participants

Reaction Steps

A stirred mixture of 53 (about 2.07 mmol), triethylamine (2.3 ml, 16.6 mmol), CH2Cl2 (21 ml) and THF (21 ml) was treated with acetyl chloride (270 mg, 3.11 mmol) and kept at ambient temperature for 18 h. It was concentrated in vacuo and the residue was mixed with saturated NaHCO3 and extracted with CH2Cl2. The extract was dried (MgSO4) and concentrated. Chromatography of the residue on silica gel with mixtures of MeOH—NH4OH—CH2Cl2 containing 2.5–10% MeOH and 0.25–1% NH4OH gave the product which was crystallized from EtOH to give 835 mg of 55: mp 178–179° C.; 1H NMR [300 MHz, (CD3)2SO] δ 1.82 (s, 3H), 2.34 (m, 4H), 2.73 (t, 2H), 2.90 3.00 (s, s, 4H), 3.22 (t, 2H), 3.39 (t, 2H), 3.55 (m, 8H), 3.66 (m, 3H), 4.07 (t, 1H), 4.69 (m, 1H), 7.07 (t, 1H), 7.17 (dd, 1H), 7.46 (m, 3H), 7.93 (d, 2H), 8.21 (t, 1H),

Provenance & Evidence