Tert-Butyl hypochlorite → HCID 86665548, compound

Participants

Reaction Steps

A solution of 3-(3-(2-(2-methoxyethoxy)ethoxy)propyl)-2,2,5,5-tetramethylimidazolidin-4-one (182 g, 0.60 mmol) in methanol (10 mL) was cooled in ice water for 10 minutes, before neat tert-butyl hypochlorite (0.10 mL, 0.9 mmol, 1.5 equiv.) was added in one portion. High pressure liquid chromatography-mass spectroscopy analysis after 5 minutes showed all starting amine had been consumed. After 20 min, the mixture was concentrated in vacuo to an oil, which was absorbed on silica (1 g). Chromatography on silica (0-4% methanol in dichloromethane) afforded the title compound as a colorless oil (193 mg, 95%). 1H NMR (400 MHz, CDCl3) δ 3.66-3.62 (m, 4H), 361-3.58 (m, 2H), 3.56-3.53 (m, 2H), 3.51 (t, J=6.0 Hz, 2H), 3.38 (s, 3H), 3.35-3.30 (m, 2H), 1.96-1.88 (m, 2H), 1.45 (s, 6H), 1.33 (s, 6H); 13C NMR (100 MHz, CDCl3) δ 172.6, 82.1, 71.9, 70.59, 70.54, 70.13, 68.6, 65.3, 59.0, 38.2, 29.1, 25.1, 23.5; LRMS (ESI/APCI) m/z 337 [M+H]+.

Provenance & Evidence