Ethyl 3-methyl-3-(trifluoromethyl)pent-4-enoate → 3-Methyl-3-(trifluoromethyl)pent-4-en-1-ol
Reaction equation
[CH3:1][C:2]([C:11]([F:14])([F:13])[F:12])([CH:9]=[CH2:10])[CH2:3][C:4](OCC)=[O:5].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C(OCC)C>[CH3:1][C:2]([C:11]([F:12])([F:14])[F:13])([CH:9]=[CH2:10])[CH2:3][CH2:4][OH:5]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Ethyl 3-methyl-3-(trifluoromethyl)pent-4-enoate (5 g, 23.8 mmol) in diethyl ether (20 mL) was added dropwise to a suspension of LAH (291 mg, 1.67 mmol) in diethyl ether (80 mL). After stirring at −78° C. for 30 min and at 0° C. for a further 30 min, the reaction mixture was quenched with sodium potassium tartrate and stirred vigorously until layers separated. The aqueous phase was extracted with diethyl ether. The combined ethereal layers were dried (magnesium sulfate) and concentrated in vacuo to afford 3-methyl-3-(trifluoromethyl)pent-4-en-1-ol which was used in the subsequent step without further purification.
Workup
- customthe reaction mixture was quenched with sodium potassium tartrate
- stirringstirred vigorously until layers
- customseparated
- extractionThe aqueous phase was extracted with diethyl ether
- dry with materialThe combined ethereal layers were dried (magnesium sulfate)
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-071d20d42ae44816b871e21d23f323ca
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08106070B2
Reaction notes
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