Fluoride Ion → 2-Hydroxy-4-phenyl-2-trifluoromethyl-valeric acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4](=[O:16])[C:5](=[O:15])[CH2:6][CH:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:8])[CH3:2].[F:17][C:18]([Si](C)(C)C)([F:20])[F:19].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[F-]>O1CCCC1.C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:16])[C:5]([OH:15])([C:18]([F:20])([F:19])[F:17])[CH2:6][CH:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:8])[CH3:2]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
4.4 g of 2-oxo-4-phenylvaleric acid ethyl ester is dissolved in 40 ml of tetrahydrofuran and mixed at −78° C. with 3.6 ml of trifluoromethyl-trimethylsilane and 2 ml of 1 M tetrabutylammonium fluoride in tetrahydrofuran. After 24 hours at −78° C., another 20 ml of 1 M tetrabutylammoinum fluoride in tetrahydrofuran is added. It is stirred for 1.5 hours at 0° C., ethyl acetate and saturated common salt solution are added, the organic phase is separated, and it is washed with saturated common salt solution and water. Then, it is dried (Na2SO4) and concentrated by evaporation and distilled on a bulb tube. 4.4 g of 2-hydroxy-4-phenyl-2-trifluoromethyl-valeric acid ethyl ester, boiling point 95-100° C./0.04 hPa, is obtained.
Workup
- customthe organic phase is separated
- washit is washed with saturated common salt solution and water
- dry with materialThen, it is dried (Na2SO4)
- concentrationconcentrated by evaporation
- distillationdistilled on a bulb tube
Sources & evidence
- ORD record
- ord-d00af51a86e14350a3699f69c1390f34
- Source dataset
- uspto-grants-2003_04
- Patent number
- US06548534B2
Reaction notes
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