Sodium hydride → trifluoromethanesulfonic acid 2,2-difluoro-1(R)-(4-fluorophenyl)-2-(4-methylsulfanylphenoxy)ethyl ester
Reaction equation
[H-].[Na+].[F:3][C:4]([F:23])([O:14][C:15]1[CH:20]=[CH:19][C:18]([S:21][CH3:22])=[CH:17][CH:16]=1)[C@@H:5]([C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1)[OH:6].[F:24][C:25]([F:31])([F:30])[S:26](Cl)(=[O:28])=[O:27]>CCCCC.C(OCC)C>[F:23][C:4]([F:3])([O:14][C:15]1[CH:20]=[CH:19][C:18]([S:21][CH3:22])=[CH:17][CH:16]=1)[C@H:5]([O:6][S:26]([C:25]([F:31])([F:30])[F:24])(=[O:28])=[O:27])[C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
NaH (60% in oil, 1.54 g, 4.9 mmol) was washed several times with pentane, under nitrogen and then suspended in anhydrous ethyl ether (10 m) and cooled at 0° C. A solution of 2,2-difluoro-1(R)-(4-fluorophenyl)-2-(4-methylsulfanylphenoxy)ethanol in ethyl ether (10 ml) was added. After stirring the reaction mixture for 15 min, trifluoromethylsulfonyl chloride was added and the resulting mixture was stirred for 2 h at 0° C. The reaction mixture was diluted with hexanes (20 ml) and washed with saturated solution of NaHCO3 and brine. After drying over magnesium sulfate, the solution was concentrated to give trifluoromethanesulfonic acid 2,2-difluoro-1(R)-(4-fluorophenyl)-2-(4-methylsulfanylphenoxy)ethyl ester (1.70 g, 77%) as an oil.
Workup
- stirringthe resulting mixture was stirred for 2 h at 0° C
- washwashed with saturated solution of NaHCO3 and brine
- dry with materialAfter drying over magnesium sulfate
- concentrationthe solution was concentrated
Sources & evidence
- ORD record
- ord-a28339415ca940a693c19407f30c7d75
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08013186B2
Reaction notes
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