Triethylamine → (E)-tert-Butyl 2-(2-methoxyethoxymethyl)-3-(p-toluenesulphonyl)acrylate

HRID 53459

反応式

HRID 53459 の反応式
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](I)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH3:12][O:13][CH2:14][CH2:15][O:16][CH2:17][C:18](=[CH2:26])[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20].C(N(CC)CC)C>ClCCl.O>[CH3:12][O:13][CH2:14][CH2:15][O:16][CH2:17]/[C:18](=[CH:26]\[S:7]([C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)(=[O:9])=[O:8])/[C:19]([O:21][C:22]([CH3:24])([CH3:23])[CH3:25])=[O:20]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 11022347p-Toluenesulphonyl iodideHCID 11096016tert-Butyl 2-(2-methoxyethoxymethyl)acrylate

生成物 1

HCID 10937543(E)-tert-Butyl 2-(2-methoxyethoxymethyl)-3-(p-toluenesulphonyl)acrylate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of p-toluenesulphonyl iodide (19.39 g, 68.7 mmol) in dichloromethane (50 mL) at room temperature under a nitrogen atmosphere was added tert-butyl 2-(2-methoxyethoxymethyl)acrylate (9.91 g, 45.8 mmol). The mixture was stirred at room temperature for 16 hours, cooled to 0° C. and triethylamine (12.7 mL, 91.6 mmol) added dropwise. The reaction was stirred at 0° C. for 0.5 hours and at room temperature for 4 hours, diluted with distilled water (100 mL) and the layers separated. The aqueous layer was further extracted with dichloromethane (25 mL) and the combined organic extracts were washed with 1.0M aqueous hydrochloric acid solution (100 mL), 5% aqueous sodium thiosulphate solution (25 mL) and distilled water (50 mL). The dichloromethane phase was concentrated under reduced pressure to give a brown oil (17.48 g, quantitative). The crude product was purified by chromatography on silica by gradient elution with hexane/ethyl acetate mixtues to give, after combination and evaporation of appropriate fractions, the title compound as a pale yellow oil (16.2 g, 95%) which crystallised on standing, m.pt.=40°-41° C., Rf =0.3 (silica; hexane/ethyl acetate, 2:1).

後処理

  1. temperaturecooled to 0° C.
  2. stirringThe reaction was stirred at 0° C. for 0.5 hours and at room temperature for 4 hours
  3. customthe layers separated
  4. extractionThe aqueous layer was further extracted with dichloromethane (25 mL)
  5. washthe combined organic extracts were washed with 1.0M aqueous hydrochloric acid solution (100 mL), 5% aqueous sodium thiosulphate solution (25 mL)
  6. distillationdistilled water (50 mL)
  7. concentrationThe dichloromethane phase was concentrated under reduced pressure
  8. customto give a brown oil (17.48 g, quantitative)
  9. customThe crude product was purified by chromatography on silica by gradient elution with hexane/ethyl acetate mixtues
  10. customto give
  11. customafter combination and evaporation of appropriate fractions
  12. customthe title compound as a pale yellow oil (16.2 g, 95%) which crystallised

出典と根拠

ORDレコード
ord-a856d0686a724180870dec869d279383
出典データセット
uspto-grants-1997_04
特許番号
US05618970

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