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

HRID 1025919ノート

反応式

HRID 1025919 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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]+.

後処理

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

出典と根拠

ORDレコード
ord-eb14a690763c47919a647f204dc86a89
出典データセット
uspto-grants-2014_05
特許番号
US08729112B2

反応ノート

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