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tert-Butoxy bis(dimethylamino)methane → 5-Dimethylaminomethylene-4-oxo-4,5,6,7-tetrahydrobenzo[b]thiophene-2-carboxylic acid tert-butyl ester

HRID 643739
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Reaktionsgleichung

Reaktionsgleichung von HRID 643739
[C:1]([O:5][C:6]([C:8]1[S:12][C:11]2[CH2:13][CH2:14][CH2:15][C:16](=[O:17])[C:10]=2[CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(O[CH:23](N(C)C)[N:24]([CH3:26])[CH3:25])(C)C>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([C:8]1[S:12][C:11]2[CH2:13][CH2:14][C:15](=[CH:23][N:24]([CH3:26])[CH3:25])[C:16](=[O:17])[C:10]=2[CH:9]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
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Komponenten

4

Edukt 2

HCID 79885tert-Butoxy bis(dimethylamino)methaneHCID 592628594-Oxo-4,5,6,7-tetrahydro-benzo[b]thiophene-2-carboxylic acid tert-butyl ester

Produkt 1

HCID 674064945-Dimethylaminomethylene-4-oxo-4,5,6,7-tetrahydrobenzo[b]thiophene-2-carboxylic acid tert-butyl esterAusbeute 58,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

4-Oxo-4,5,6,7-tetrahydro-benzo[b]thiophene-2-carboxylic acid tert-butyl ester (8.75 g, 34.68 mmol) was suspended in dry toluene (40 mL) and Bredereck's reagent (6.65 g, 38.14 mmol) was added. The resulting suspension was heated at reflux for 2 hours, during which time all starting material dissolved, allowed to cool to room temperature and concentrated under reduced pressure. The resulting oil was purified by silica gel chromatography (50% EtOAc in hexanes on 1 L silica, loaded as a solution in dichloromethane) to afford the title compound as a brown solid (6.21 g, 58% yield). MS (ES+) 308. δH (CDCl3) 1.5-1.6 (9H, s), 2.9-3.0 (2H, m), 3.0-3.1 (2H, m), 3.1 (6H, s), 7.6 (1H, s), 8.0 (1H, s).

Aufarbeitung

  1. temperatureThe resulting suspension was heated
  2. temperatureat reflux for 2 hours, during which time all starting material
  3. dissolutiondissolved
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting oil was purified by silica gel chromatography (50% EtOAc in hexanes on 1 L silica

Quellen und Nachweise

ORD-Eintrag
ord-f38af129a6924e268c9623f6eb3dbce1
Quelldatensatz
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07700609B2

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