2,2,2-Trifluoroethanol → HCID 17956302, compound
Reaction equation
[CH2:1]([OH:6])[C:2]([F:5])([F:4])[F:3].[H-].[Na+].CC1C=CC(S(O[CH2:20][CH2:21][O:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][O:31][CH2:32][CH2:33][O:34][CH2:35][CH2:36][O:37][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)(=O)=O)=CC=1>O1CCCC1>[F:3][C:2]([F:5])([F:4])[CH2:1][O:6][CH2:20][CH2:21][O:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][O:31][CH2:32][CH2:33][O:34][CH2:35][CH2:36][O:37][CH2:38][C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
To a stirred solution of trifluoroethanol (0.1 g) and sodium hydride (60% dispersion in mineral oil; (0.05 g) in tetrahydrofuran (10 ml) was added the product of step (b) (0.5 g) and the reaction stirred for 24 hours at 20° C. The reaction was quenched by the addition of methanol (5 ml) and the solvent removed in vacuo. The residue was partitioned between ethyl acetate (50 ml) and water (50 ml). The organic layer was washed with brine (50 ml), dried and the solvent removed in vacuo. Purification by column chromatography on silica gel (Biotage), eluting with 50% ethyl acetate in cyclohexane gave the title compound (0.27 g).
Workup
- customThe reaction was quenched by the addition of methanol (5 ml)
- customthe solvent removed in vacuo
- customThe residue was partitioned between ethyl acetate (50 ml) and water (50 ml)
- washThe organic layer was washed with brine (50 ml)
- customdried
- customthe solvent removed in vacuo
- customPurification by column chromatography on silica gel (Biotage)
- washeluting with 50% ethyl acetate in cyclohexane
Sources & evidence
- ORD record
- ord-b39d28be4b514473a712d443e58d5da7
- Source dataset
- uspto-grants-2008_04
- Patent number
- US07354966B2
Reaction notes
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