Tert-Butyl hypochlorite → 1-Chloro-3-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)-2,2,5,5-tetramethylimidazolidin-4-one

HRID 1770726ノート

反応式

HRID 1770726 の反応式
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][N:11]1[C:15](=[O:16])[C:14]([CH3:18])([CH3:17])[NH:13][C:12]1([CH3:20])[CH3:19].C(O[Cl:26])(C)(C)C>CO>[Cl:26][N:13]1[C:14]([CH3:18])([CH3:17])[C:15](=[O:16])[N:11]([CH2:10][CH2:9][O:8][CH2:7][CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])[C:12]1([CH3:20])[CH3:19]

参加物

4

反応物 2

HCID 521297Tert-Butyl hypochloriteHCID 675080933-(2-(2-(2-Methoxyethoxy)ethoxy)ethyl)-2,2,5,5-tetramethylimidazolidin-4-one

生成物 1

HCID 569663761-Chloro-3-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)-2,2,5,5-tetramethylimidazolidin-4-one収率 92%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

To a 0° C. solution of 3-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)-2,2,5,5-tetramethylimidazolidin-4-one (15.03 g, 52.1 mmol) in methanol (150 ml) was added tert-butylhypochlorite (8.50 g of 0.91 g/mL, 78.3 mmol), over a 10 minute period. The mixture was stirred for 1 hour at 0° C. The reaction mixture was checked for completion by high pressure liquid chromatography. The reaction mixture was concentrated in vacuo, and crude material was purified by silica gel flash chromatography (0 to 10% methanol in dichloromethane) to give 15.43 g (92%) of the title compound. 1H NMR (D2O, 400 MHz) δ 3.74-3.65 (m, 8H), 3.62-3.60 (m, 2H), 3.55 (t, J=6 Hz, 2H), 3.37 (s, 3H), 1.53 (s, 6H), 1.36 (s, 6H). 13C NMR (D2O, 100 MHz) δ 175.00, 83.68, 70.98, 69.59 (2 peaks), 69.39, 67.65, 66.02, 57.99, 40.16, 24.07, 22.52. LRMS (ESI/APCI) m/z 323 [M+H]+.

後処理

  1. concentrationThe reaction mixture was concentrated in vacuo, and crude material
  2. customwas purified by silica gel flash chromatography (0 to 10% methanol in dichloromethane)

出典と根拠

ORDレコード
ord-3f0a1a5932794f40a8809a35423c6bcb
出典データセット
uspto-grants-2016_02
特許番号
US09248117B2

反応ノート

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