Dimethylformamide → 1-Hydroxy-3-(2,2,2-trifluoroethylthio)-prop-2-ene
Reaction equation
[F:1][C:2]([F:6])([F:5])[CH2:3][SH:4].[CH2:7]([OH:10])[C:8]#[CH:9].[OH-].[K+].CN(C)C=O>O>[OH:10][CH2:7][CH:8]=[CH:9][S:4][CH2:3][C:2]([F:6])([F:5])[F:1]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 2.32 g 2,2,2-trifluoroethanethiol, 1.12 prop-2-yne-1-ol, 300 mg potassium hydroxide and 40 ml dimethylformamide is stirred at ambient temperature for 20 hours. The mixture is poured into 150 ml of water and extracted with 100 ml ethyl acetate (3 times). The organic phase is washed with water, dried and concentrated. The crude product is purified by column chromatography to obtain 75 mg of pure 1-hydroxy-3-(2,2,2-trifluoroethylthio)-prop-2-ene.
Workup
- extractionextracted with 100 ml ethyl acetate (3 times)
- washThe organic phase is washed with water
- customdried
- concentrationconcentrated
- customThe crude product is purified by column chromatography
Sources & evidence
- ORD record
- ord-a4e31eede09542dc982fa294b47e544c
- Source dataset
- uspto-grants-2003_03
- Patent number
- US06534447B1
Reaction notes
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