Triethylamine → Ethyl 4-(4,4,4-trifluorobutanoyl)benzoate
Reaction equation
[F:1][C:2]([F:19])([F:18])[CH2:3][CH2:4][CH:5]([C:7]1[CH:17]=[CH:16][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][CH:8]=1)[OH:6].C(N(CC)CC)C>ClCCl.CS(C)=O>[F:1][C:2]([F:18])([F:19])[CH2:3][CH2:4][C:5]([C:7]1[CH:17]=[CH:16][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][CH:8]=1)=[O:6]Participants
5
Conditions
- Temperature
- 0 °C
Procedure
A mixture of (+/−)-ethyl 4-(4,4,4-trifluoro-1-hydroxybutyl)benzoate (2.10 g, 7.60 mmol) in dichloromethane (28 ml), dimethyl sulfoxide (22 ml), and triethylamine (5.29 ml, 38.0 mmol) was cooled to 0° C. Sulfur trioxide pyridine complex (3.63 g, 22.8 mmol) was added in portions and the mixture stirred at 0° C. for 1 hour, then slowly raised to ambient temperature over 12 h. The reaction was quenched with water and diluted with diethylether. The aqueous layer was extracted with diethylether and the combined organic layers were washed with brine. The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated in vacuo to affording the crude product as a solid that was used without further purification.
Workup
- additionSulfur trioxide pyridine complex (3.63 g, 22.8 mmol) was added in portions
- temperatureslowly raised to ambient temperature over 12 h
- customThe reaction was quenched with water
- additiondiluted with diethylether
- extractionThe aqueous layer was extracted with diethylether
- washthe combined organic layers were washed with brine
- dry with materialThe combined organic extracts were dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-2daeaa805b5342fdb60fe2816b40a0ae
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08507533B2
Reaction notes
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