Trifluoroacetic acid → HCID 53813302, compound
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]2[O:18][C:17](=O)[CH:16]([CH2:20][CH2:21][CH3:22])[CH2:15][CH2:14]2)[CH:5]=[C:6]([F:12])[C:7]=1[C:8]([F:11])([F:10])[F:9].C([SiH](CC)CC)C.FC(F)(F)C(O)=O>O>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:13]2[CH2:14][CH2:15][C@H:16]([CH2:20][CH2:21][CH3:22])[CH2:17][O:18]2)[CH:5]=[C:6]([F:12])[C:7]=1[C:8]([F:9])([F:10])[F:11]Participants
Procedure
A mixture of 7.7 g (22.7 mmol) of the 6-(3-chloro-5-fluoro-4-trifluoromethylphenyl)-3-propyltetrahydro-2-pyrone, 13.2 g (113.6 mmol) of triethylsilane, and 50 ml of trifluoroacetic acid was stirred at room temperature for 1 hour. After termination of the reaction, 30 ml of water was added to the reaction solution and extracted with 50 ml of toluene. The organic layer thus obtained was washed with a diluted aqueous sodium bicarbonate solution thrice and water thrice, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under a reduced pressure and the residue was subjected to silica gel column chromatography (eluent: heptane/toluene=9/1) to obtain 6.6 g of a crude trans-2-(3-chloro-5-fluoro-4-trifluoromethylphenyl)-5-propyltetrahydropyran.
Workup
- additionwas added to the reaction solution
- extractionextracted with 50 ml of toluene
- customThe organic layer thus obtained
- washwas washed with a diluted aqueous sodium bicarbonate solution thrice and water thrice
- dry with materialdried over anhydrous magnesium sulfate
- distillationThe solvent was distilled off under a reduced pressure
Sources & evidence
- ORD record
- ord-98c91ba0aed84012a81fd2b97a469d90
- Source dataset
- uspto-grants-2001_12
- Patent number
- US06329027B1
Reaction notes
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