Hydrochloric Acid → 6-(3-Chloro-5-fluoro-4-trifluoromethylphenyl)-3-propyltetrahydro-2-pyrone
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]([OH:23])[CH2:14][CH2:15][CH:16]([CH2:20][CH2:21][CH3:22])[C:17]([O-:19])=O)[CH:5]=[C:6]([F:12])[C:7]=1[C:8]([F:11])([F:10])[F:9].Cl.C(O)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]2[O:23][C:17](=[O:19])[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:9])([F:10])[F:11]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 12.0 g (31.2 mmol) of ethyl=5-(3-chloro-5-fluoro-4-trifluoromethylphenyl)-5-hydroxy-2-propylpentanoate [prepared by reacting 3-propyl-5-formylpentanoic acid with 3-chloro-5-fluoro-4-trifluromethylphenylmagnesium bromide], 25 ml of a concentrated hydrochloric acid, and 100 ml of ethanol was heated at 50° C. while being stirred for 3 hours. To the reaction solution was added 50 ml of toluene, and 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 chromatography (eluent: heptane/toluene=1/1) to obtain 7.7 g of a crude 6-(3-chloro-5-fluoro-4-trifluoromethylphenyl)-3-propyltetrahydro-2-pyrone. (Yield: 73.3%)
Workup
- 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-5bd9c54792584dc7bf022aed177ee9d8
- Source dataset
- uspto-grants-2001_12
- Patent number
- US06329027B1
Reaction notes
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