Hexafluoroacetone → 1,1,1-Trifluoro-2-trifluoromethyl-but-3-yn-2-ol
Reaction equation
[C:1]([Mg]Br)#[CH:2].[F:5][C:6]([F:14])([F:13])[C:7]([C:9]([F:12])([F:11])[F:10])=[O:8]>>[F:5][C:6]([F:14])([F:13])[C:7]([C:9]([F:12])([F:11])[F:10])([OH:8])[C:1]#[CH:2]Participants
3
Procedure
To a 100 ml solution of ethynyl magnesium bromide (0.5 M in THF) in an acetone-ethanol dry ice bath was bubbled hexafluoro acetone gas (6.1 g, 36.7 mmol) over 2 h. The reaction mixture was warmed to r.t and then refluxed for 0.5 h. The reaction mixture was quenched with aqueous NH4Cl solution and extracted with ether. The combined organic phases were washed with brine, and dried over MgSO4. A liquid mixture of 1,1,1-trifluoro-2-trifluoromethyl-but-3-yn-2-ol with THF at b.p. 100-103° C. (4.7 g, contained about 68 mol % THF) was obtained by distillation (12 inch Vigreux column).
Workup
- temperatureThe reaction mixture was warmed
- temperaturerefluxed for 0.5 h
- customThe reaction mixture was quenched with aqueous NH4Cl solution
- extractionextracted with ether
- washThe combined organic phases were washed with brine
- dry with materialdried over MgSO4
- additionA liquid mixture of 1,1,1-trifluoro-2-trifluoromethyl-but-3-yn-2-ol with THF at b.p. 100-103° C. (4.7 g, contained about 68 mol % THF)
- customwas obtained by distillation (12 inch Vigreux column)
Sources & evidence
- ORD record
- ord-bc0f9e64dc2c410f9952536a047ea73f
- Source dataset
- uspto-grants-2012_02
- Patent number
- US08119819B2
Reaction notes
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