HCID 20153884, compound → 2-[4-tert-Butylphenyl]prop-2-en-1-yl acetate

HRID 607521Notes

Reaction equation

[CH3:1]C(C)([O-])C.[K+].[C:7]([O:10][CH2:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:16][CH:15]=1)=O)(=[O:9])[CH3:8]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[C:7]([O:10][CH2:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:16][CH:15]=1)=[CH2:1])(=[O:9])[CH3:8]

Participants

Conditions

Temperature: 40 °C

Procedure

To a stirred suspension of methyltriphenylphosphonium bromide (8.48 g, 23.7 mmol) in THF (75 ml) was added potassium tert-butoxide (2.66 g, 23.7 mmol) at room temperature. The mixture was stirred at 40° C. for 1 hour. After cooling to room temperature, a solution of 2-[4-tert-butylphenyl]-2-oxoethyl acetate (U.S. Pat. No. 3,526,634, 2.78 g, 11.9 mmol) in THF (25 ml) was added to the mixture. The mixture was heated at reflux for 3 hours. The mixture was concentrated, diluted with EtOAc and washed with water and brine. The organic layer was dried over sodium sulfate and concentrated in vacuo. The crude material was purified by silica gel column chromatography, eluting with hexane/EtOAc (9:1), to afford the title compound (2.13 g, 77%) as a yellow oil.

Workup

temperatureAfter cooling to room temperature
temperatureThe mixture was heated
temperatureat reflux for 3 hours
concentrationThe mixture was concentrated
additiondiluted with EtOAc
washwashed with water and brine
dry with materialThe organic layer was dried over sodium sulfate
concentrationconcentrated in vacuo
customThe crude material was purified by silica gel column chromatography
washeluting with hexane/EtOAc (9:1)

Sources & evidence

ORD record: ord-c5fdd3c1ee3b400fa9f997d1d77d8af5
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07915448B2

Reaction notes

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