Triethylamine → 1-Fluoro-2-fluoromethyl-3-butyn-2-yl methanesulfonate
Reaction equation
[F:1][CH2:2][C:3]([CH2:7][F:8])([OH:6])[C:4]#[CH:5].[CH3:9][S:10](Cl)(=[O:12])=[O:11].C(N(CC)CC)C>COC(C)(C)C>[CH3:9][S:10]([O:6][C:3]([CH2:7][F:8])([C:4]#[CH:5])[CH2:2][F:1])(=[O:12])=[O:11]Participants
5
Procedure
An amount (1.2 g) of 1-fluoro-2-fluoromethyl-3-butyn-2-ol and methanesulfonyl chloride (0.85 ml) were dissolved in tert-butyl methyl ether (15 ml); to the solution under cooling with ice, triethylamine (1.5 ml) was added dropwise in a nitrogen atmosphere. After the end of the dropwise addition, the solution was stirred for 1.5 hours under cooling with ice. To the reaction mixture, tert-butyl methyl ether was added, followed by washing with water and a saturated aqueous solution of sodium chloride. The mixture was dried with anhydrous sodium sulfate and concentrated under reduced pressure to give the titled compound (1.9 g).
Workup
- additionwas added dropwise in a nitrogen atmosphere
- additionAfter the end of the dropwise addition
- temperatureunder cooling with ice
- washby washing with water
- dry with materialThe mixture was dried with anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-c9e73eaf23854d7bb8aa2a2b0fc6d320
- Source dataset
- uspto-grants-2002_09
- Patent number
- US06455708B1
Reaction notes
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