Triethylamine → 2-[2-(2,2,2-Trifluoroethoxy)phenoxy]ethyl Methanesulfonate
Reaction equation
[F:1][C:2]([F:16])([F:15])[CH2:3][O:4][C:5]1[CH:14]=[CH:13][CH:12]=[CH:11][C:6]=1[O:7][CH2:8][CH2:9][OH:10].C(N(CC)CC)C.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>C(Cl)Cl>[CH3:24][S:25]([O:10][CH2:9][CH2:8][O:7][C:6]1[CH:11]=[CH:12][CH:13]=[CH:14][C:5]=1[O:4][CH2:3][C:2]([F:15])([F:16])[F:1])(=[O:27])=[O:26]Participants
Procedure
To a solution of 2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethanol (210 mg) in methylene chloride (1 ml) were added triethylamine (186 μl) and methanesulfonyl chloride (83 μl) with stirring under ice cooling, and the mixture was reacted at room temperature for 30 minutes. The reaction mixture was concentrated under reduced pressure. To the concentrate was added water, and the mixture was extracted with diethyl ether. The extract was washed with water, dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by medium pressure liquid column chromatography on silica gel using a mixture of hexane and ethyl acetate (2/1) as eluent to give 273 mg of 2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl methansulfonate melting at 40.5°-42.0° C.
Workup
- customthe mixture was reacted at room temperature for 30 minutes
- concentrationThe reaction mixture was concentrated under reduced pressure
- additionTo the concentrate was added water
- extractionthe mixture was extracted with diethyl ether
- washThe extract was washed with water
- dry with materialdried over anhydrous magnesium sulfate
- customThe solvent was evaporated under reduced pressure
- customthe residue was purified by medium pressure liquid column chromatography on silica gel using
- additiona mixture of hexane and ethyl acetate (2/1) as eluent
Sources & evidence
- ORD record
- ord-68eaa92338f647288ba099d25bf70c98
- Source dataset
- uspto-grants-1995_02
- Patent number
- US05387603
Reaction notes
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