Sodium hydride → 2-(4-methanesulfonylbenzyl)-3-oxothiobutyric acid S-tert-butyl Ester

HRID 2266499Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2266499
[C:1]([S:5][C:6](=[O:11])[CH2:7][C:8](=[O:10])[CH3:9])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:17]=1>COCCOC.[Cl-].[NH4+]>[C:1]([S:5][C:6](=[O:11])[CH:7]([CH2:15][C:16]1[CH:17]=[CH:18][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:20][CH:21]=1)[C:8](=[O:10])[CH3:9])([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 140007Butanethioic acid, 3-oxo-, S-(1,1-dimethylethyl) esterHCID 27335814-(Methylsulfonyl)benzyl Bromide

Produkt 1

HCID 866314382-(4-methanesulfonylbenzyl)-3-oxothiobutyric acid S-tert-butyl Ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 80711,2-DimethoxyethaneLösungsmittel3×HCID 25517Ammonium ChlorideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 3-oxothiobutyric acid S-tert-butyl ester (7.5 g) in 1,2-dimethoxyethane (10 mL) was added to a stirred suspension of sodium hydride (60% in oil, 1.9 g) in 1,2-dimethoxyethane (100 mL) at −20° C. The mixture was warmed to 0° C. for 10 minutes and then a solution of 1-bromomethyl-4-methanesulfonylbenzene (12.9 g) in 1,2-dimethoxyethane (30 mL) was added dropwise over a period of 10 minutes. The resulting mixture was warmed to room temperature over 30 minutes and then stirred at this temperature for 17 hours. The mixture was diluted with saturated aqueous ammonium chloride solution (70 mL) and the phases separated. The aqueous phase was extracted with diethyl ether and the combined organic phases were dried over magnesium sulfate. The solvent was removed under reduced pressure and purification of the residue by column chromatography on silica gel, eluting with a mixture of dichloromethane and ethyl acetate (1:0 to 4:1 by volume) gave title compound, 7.1 g.

Aufarbeitung

  1. temperatureThe resulting mixture was warmed to room temperature over 30 minutes
  2. customthe phases separated
  3. extractionThe aqueous phase was extracted with diethyl ether
  4. dry with materialthe combined organic phases were dried over magnesium sulfate
  5. customThe solvent was removed under reduced pressure and purification of the residue by column chromatography on silica gel
  6. washeluting with a mixture of dichloromethane and ethyl acetate (1:0 to 4:1 by volume)

Quellen und Nachweise

ORD-Eintrag
ord-559e7a9e997f4b87a5994f3c9ada7549
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07858640B2

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