Tert-Butyl hypochlorite → 3-Chloro-4-(chloromethyl)-4-methyloxazolidin-2-one

HRID 1025919노트

반응식

HRID 1025919 반응식
[Cl:1][CH2:2][C:3]1([CH3:9])[CH2:7][O:6][C:5](=[O:8])[NH:4]1.C(O[Cl:15])(C)(C)C>CO>[Cl:15][N:4]1[C:3]([CH2:2][Cl:1])([CH3:9])[CH2:7][O:6][C:5]1=[O:8]

참가 물질

4

반응물 2

HCID 521297Tert-Butyl hypochloriteHCID 553038834-Chloromethyl-4-methyl-oxazolidin-2-one

생성물 1

HCID 569618563-Chloro-4-(chloromethyl)-4-methyloxazolidin-2-one

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A solution of 4-(chloromethyl)-4-methyloxazolidin-2-one (13.39 g, 89.52 mmol) in MeOH (100 ml) was cooled to 0° C., and tert-butylhypochlorite (12.0 ml, 101 mmol) was added dropwise over 15 min. The solution was warmed to RT over 45 min, and concentrated in vacuo. The residue was crystallized by dissolution in ˜80 ml CH2Cl2 followed by careful layering of 60 ml hexanes to afford the title compound as white, fan-shaped crystals (12.31 g, 66.89 mmol, 75%). 1H NMR (CDCl3, 400 MHz) δ1.50 (s, 3H), 3.55 (d, J=12.0 Hz, 1H), 3.75 (d, J=12.0 Hz, 1H), 4.19 (d, J=8.8 Hz, 1H), 4.53 (d, J=8.4 Hz, 1H). 13C NMR (CDCl3, 100 MHz) δ 20.4, 46.7, 64.1, 155.7. LRMS (ESI/APCI): 225 [M+H+CH3CN]+, 191 [M+H−Cl+CH3CN]+, 184 [M+H]+, 150 [M+H−Cl]+.

후처리

  1. concentrationconcentrated in vacuo
  2. customThe residue was crystallized by dissolution in ˜80 ml CH2Cl2

출처 및 근거

ORD 기록
ord-eb14a690763c47919a647f204dc86a89
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08729112B2

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