tert-Butanol → HCID 66717606, compound

HRID 2266519Notes

Reaction equation

CC(C)([O-])C.[K+].C(O)(C)(C)C.[CH2:12]([O:14][C:15](=[O:21])[CH2:16][C:17](=[O:20])[CH2:18][CH3:19])[CH3:13].Br[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=1>O1CCCC1.O>[CH2:12]([O:14][C:15](=[O:21])[CH:16]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=1)[C:17](=[O:20])[CH2:18][CH3:19])[CH3:13]

Participants

Conditions

Temperature: 70 °C

Procedure

A suspension of potassium tert-butoxide (2.8 g) in anhydrous tetrahydrofuran (400 mL) at 0° C. was treated with a mixture of tert-butanol (1.0 mL) and 3-oxopentanoic acid ethyl ester (3.0 g). After stirring at room temperature for 45 minutes a solution of 1-bromomethyl-4-chlorobenzene (4.3 g) in tetrahydrofuran (100 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. The residue was purified by column chromatography on silica gel, eluting with a mixture of cyclohexane and methyl tert-butyl ether (4:1 by volume) to afford title compound. 4.8 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
customThe residue was purified by column chromatography on silica gel
washeluting with a mixture of cyclohexane and methyl tert-butyl ether (4:1 by volume)

Sources & evidence

ORD record: ord-6ef18931e53046829cc27cf31c8064df
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858640B2

Reaction notes

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