ethyl (E)-5-[4-(trifluoromethyl)phenyl]-2-penten-4-ynoate → (E)-5-[4-(Trifluoromethyl)phenyl]-2-penten-4-yn-1-ol

HRID 379955Notes

Reaction equation

[F:1][C:2]([F:19])([F:18])[C:3]1[CH:8]=[CH:7][C:6]([C:9]#[C:10]/[CH:11]=[CH:12]/[C:13](OCC)=[O:14])=[CH:5][CH:4]=1.[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1>C1(C)C=CC=CC=1>[F:1][C:2]([F:18])([F:19])[C:3]1[CH:4]=[CH:5][C:6]([C:9]#[C:10]/[CH:11]=[CH:12]/[CH2:13][OH:14])=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 0 °C

Procedure

In 4 ml of toluene were dissolved 480 mg (1.79 mmol) of ethyl (E)-5-[4-(trifluoromethyl)phenyl]-2-penten-4-ynoate, and 2.38 ml (3.58 mmol) of a 1.5M diisobutyl aluminum hydride-toluene solution were added to the solution with stirring at 0° C. After 10 minutes, ice was added to the mixture and the insolubles were removed by filtration using Celite. After the organic layer was dried, the crude product obtained by evaporation of the solvent was subjected to column chromatography using 15 g of silica gel and eluted with a mixed solvent of ethyl acetate-hexane (3:17) to obtain 353 mg (yield: 87%) of the title compound as an oil.

Workup

additionwere added to the solution
additionice was added to the mixture
customthe insolubles were removed by filtration
customAfter the organic layer was dried
customthe crude product obtained by evaporation of the solvent
washeluted with a mixed solvent of ethyl acetate-hexane (3:17)

Sources & evidence

ORD record: ord-3c0d32b591254132be54c65fe4804522
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06300357B1

Reaction notes

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