tert-Butanol → 2-(4-methanesulfonylbenzyl)-3-oxobutyric Acid Ethyl Ester

HRID 2266476Notes

Reaction equation

CC(C)([O-])C.[K+].C(O)(C)(C)C.[CH2:12]([O:14][C:15](=[O:20])[CH2:16][C:17](=[O:19])[CH3:18])[CH3:13].Br[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:25][CH:24]=1>O1CCCC1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[CH2:12]([O:14][C:15](=[O:20])[CH:16]([CH2:22][C:23]1[CH:24]=[CH:25][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:27][CH:28]=1)[C:17](=[O:19])[CH3:18])[CH3:13]

Participants

Conditions

Temperature: 70 °C

Procedure

A suspension of potassium tert-butoxide (4.5 g) in anhydrous tetrahydrofuran (70 mL) at 0° C. was treated with a mixture of tert-butanol (0.2 mL) and 3-oxobutyric acid ethyl ester (5.2 g). After stirring at 15° C. for 15 minutes a solution of 1-bromomethyl-4-methanesulfonylbenzene (10 g) in tetrahydrofuran (30 mL) was added and the resulting mixture heated at 70° C. for 17 hours. The mixture was diluted with saturated aqueous citric acid solution (20 mL) and extracted with ethyl acetate. The combined extracts were washed with saturated aqueous sodium chloride solution and dried over magnesium sulfate. The solvent was removed under reduced pressure and the residue purified by column chromatography on silica gel, eluting with a mixture of pentane and dichloromethane (2:1 to 0:1 by volume) to afford title compound as a gum, 3.5 g.

Workup

additionwas added
extractionextracted with ethyl acetate
washThe combined extracts were washed with saturated aqueous sodium chloride solution
dry with materialdried over magnesium sulfate
customThe solvent was removed under reduced pressure
customthe residue purified by column chromatography on silica gel
washeluting with a mixture of pentane and dichloromethane (2:1 to 0:1 by volume)

Sources & evidence

ORD record: ord-d355b4c00d4b4742af19560c8ee8cc27
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858640B2

Reaction notes

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