Propionic Acid → Ethyl 3-methyl-3-(trifluoromethyl)pent-4-enoate

HRID 425322

Reaction equation

[CH:1]([O:8]CC)([O:5][CH2:6][CH3:7])OCC.[F:11][C:12]([F:19])([F:18])[C:13]([CH3:17])=[CH:14][CH2:15]O.[C:20](O)(=O)CC>C(OCC)C>[CH3:17][C:13]([C:12]([F:19])([F:18])[F:11])([CH:14]=[CH2:15])[CH2:20][C:1]([O:5][CH2:6][CH3:7])=[O:8]

Participants

Conditions

Temperature: 200 °C

Procedure

Triethyl orthoformate (6.51 mL, 35.7 mmol) was added to an ambient temperature mixture of 4,4,4-trifluoro-3-methylbut-2-en-1-ol (500 mg, 3.57 mmol) and propionic acid (13 μL, 0.18 mmol). After heating in a sealed tube at 200° C. for 30 h, the reaction mixture was cooled, diluted with diethyl ether and washed with saturated aqueous sodium bicarbonate. The organic phase was dried (magnesium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 0-20% ethyl acetate/hexane afforded ethyl 3-methyl-3-(trifluoromethyl)pent-4-enoate.

Workup

temperaturethe reaction mixture was cooled
washwashed with saturated aqueous sodium bicarbonate
dry with materialThe organic phase was dried (magnesium sulfate)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-9b9a5bb07d734710b59aedda91ab7793
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08106070B2

Linked notes

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