Triethylamine → (E)-tert-Butyl 2-(2-methoxyethoxymethyl)-3-(4-nitrobenzenesulphonyl)acrylate

HRID 53462

反応式

HRID 53462 の反応式
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10](I)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:14][O:15][CH2:16][CH2:17][O:18][CH2:19][C:20](=[CH2:28])[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22].C(N(CC)CC)C>ClCCl.O>[CH3:14][O:15][CH2:16][CH2:17][O:18][CH2:19]/[C:20](=[CH:28]\[S:10]([C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)(=[O:12])=[O:11])/[C:21]([O:23][C:24]([CH3:26])([CH3:25])[CH3:27])=[O:22]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 11096016tert-Butyl 2-(2-methoxyethoxymethyl)acrylateHCID 222536394-Nitrobenzenesulphonyl iodide

生成物 1

HCID 86750696(E)-tert-Butyl 2-(2-methoxyethoxymethyl)-3-(4-nitrobenzenesulphonyl)acrylate収率 96.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of 4-nitrobenzenesulphonyl iodide (1.49 g, 4.65 mmol) in dichloromethane (6 mL) at room temperature was added tert-butyl 2-(2-methoxyethoxymethyl)acrylate (0.68 g, 3.1 mmol). The mixture was stirred at room temperature for 3.5 hours and triethylamine (0.88 mL, 6.2 mmol) added dropwise. The reaction was stirred for 16 hours, diluted with distilled water (25 mL) and dichloromethane (10 mL) and the layers separated. The aqueous layer was further extracted with dichloromethane (5 mL) and the combined organic extracts were washed with 1.0N aqueous hydrochloric acid solution (20 mL), 5% aqueous sodium thiosulphate solution (20 mL) and distilled water (20 mL). The dichloromethane phase was dried (MgSO4), filtered and concentrated under reduced pressure to give a brown oil (1.20 g). The crude product was purified by chromatography on silica by gradient elution with hexane/ethyl acetate mixtures to give, after combination and evaporation of appropriate fractions, the title compound as a yellow oil (0.78 g, 61.9%), Rf =0.33 (silica; hexane/ethyl acetate, 2:1), (MH+ 402.88, 1.07%).

後処理

  1. stirringThe reaction was stirred for 16 hours
  2. customthe layers separated
  3. extractionThe aqueous layer was further extracted with dichloromethane (5 mL)
  4. washthe combined organic extracts were washed with 1.0N aqueous hydrochloric acid solution (20 mL), 5% aqueous sodium thiosulphate solution (20 mL)
  5. distillationdistilled water (20 mL)
  6. dry with materialThe dichloromethane phase was dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-c6626b5bbbca4fb79fe2c4bd3d8677fc
出典データセット
uspto-grants-1997_04
特許番号
US05618970

関連ノート

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