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

HRID 53462

Reaktionsgleichung

Reaktionsgleichung von HRID 53462
[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]

Komponenten

6

Edukt 3

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

Produkt 1

HCID 86750696(E)-tert-Butyl 2-(2-methoxyethoxymethyl)-3-(4-nitrobenzenesulphonyl)acrylateAusbeute 96,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-c6626b5bbbca4fb79fe2c4bd3d8677fc
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05618970

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