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

HRID 2266530Notes

Reaction equation

CC(C)([O-])C.[K+].C(O)(C)(C)C.[CH2:12]([O:14][C:15](=[O:22])[CH2:16][C:17](=[O:21])[CH:18]([CH3:20])[CH3:19])[CH3:13].Br[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([S:31]([CH3:34])(=[O:33])=[O:32])=[CH:27][CH:26]=1>O1CCCC1.O>[CH2:12]([O:14][C:15](=[O:22])[CH:16]([CH2:24][C:25]1[CH:26]=[CH:27][C:28]([S:31]([CH3:34])(=[O:33])=[O:32])=[CH:29][CH:30]=1)[C:17](=[O:21])[CH:18]([CH3:19])[CH3:20])[CH3:13]

Participants

Conditions

Temperature: 70 °C

Procedure

A suspension of potassium tert-butoxide (0.54 g) in anhydrous tetrahydrofuran (200 mL) at 0° C. was treated with a mixture of tert-butanol (0.1 mL) and 4-methyl-3-oxopentanoic acid ethyl ester (0.65 mL). After stirring at room temperature for 45 minutes a solution of 1-bromomethyl-4-methanesulfonylbenzene (1.0 g) in tetrahydrofuran (50 mL) was added and the resulting mixture heated at 70° C. for 24 hours. The mixture was cooled to room temperature, diluted with water and the tetrahydrofuran removed under reduced pressure. The residue was extracted with ethyl acetate and the combined extracts dried over magnesium sulfate and then the solvent removed under reduced pressure to afford title compound, 1.4 g.

Workup

additionwas added
temperatureThe mixture was cooled to room temperature
customthe tetrahydrofuran removed under reduced pressure
extractionThe residue was extracted with ethyl acetate
dry with materialthe combined extracts dried over magnesium sulfate
customthe solvent removed under reduced pressure

Sources & evidence

ORD record: ord-b0e2ec5922b440889a4d0586b6e47169
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858640B2

Reaction notes

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