Dimethylformamide → 1-Hydroxy-3-(2,2,2-trifluoroethylthio)-prop-2-ene

HRID 1861592Notes

Reaction equation

HRID 1861592 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

HCID 6228DimethylformamideHCID 7859Propargyl alcoholHCID 14797Potassium HydroxideHCID 41339242,2,2-Trifluoroethanethiol

Product 1

HCID 734539691-Hydroxy-3-(2,2,2-trifluoroethylthio)-prop-2-ene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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

  1. extractionextracted with 100 ml ethyl acetate (3 times)
  2. washThe organic phase is washed with water
  3. customdried
  4. concentrationconcentrated
  5. 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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