Methanol → HCID 14552599, compound

Participants

Reaction Steps

To ethyl N-{2-[4-(3-methyl-2-butenoxy)phenoxy]ethyl}-carbamate (0.60 g, 2.05 mmol) in methanol (7 ml) at ~40° is added mercuric acetate (0.67 g, 2.1 mmol) in methanol (8 ml) over 10 min. The mixture is stirred at 5° for 1 hour, then at 10°-15° for 30 min. Additional mercuric acetate (0.13 g, 0.41 mol) in methanol is added, and the mixture is allowed to stand at RT overnight. The mixture is then cooled to 3° and potassium hydroxide (0.57 g, 10.2 mmol) in methanol (4 ml) is added over 5 min., followed by addition of sodium borohydride (0.039 g, 1.02 mmol) in portions over 10 min. The resulting slurry is stirred at 3-5° for 45 min. Celite is added to the reaction mixture and the mercury is filtered off. Methanol is removed by rotoevaporation and ether and water are added to the residue. Following extraction with ether (3X), the ether extracts are combined and washed with water until neutral and with brine and dried over calcium sulfate. The crude product is filtered, rotoevaporated and purified by prep. TLC to yield ethyl N-{2-[4-(3-methoxy-3-methylbutoxy)phenoxy]ethyl }carbamate (compound 12, Table A).

Provenance & Evidence