Water → But-3-yn-2-yl methanesulfonate
Reaction equation
[CH3:1][CH:2]([OH:5])[C:3]#[CH:4].[CH3:6][S:7](Cl)(=[O:9])=[O:8].O>C(Cl)Cl>[CH3:6][S:7]([O:5][CH:2]([C:3]#[CH:4])[CH3:1])(=[O:9])=[O:8]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 5 °C
Procedure
But-3-yn-2-ol (25 ml, 317 mmol) was dissolved in DCM (6 vol) under nitrogen atmosphere. TEA (66 ml, 475.5 mmol) was added and the mixture was cooled to 5° C. Methanesulfonyl chloride (29 ml, 380.4 mmol) was added drop-wise. The reaction was then allowed to warm up to RT and the stirring was continued overnight. The reaction mixture was then poured into water, and extracted with DCM (twice). The collected organic phases were washed with a saturated solution of NaHCO3, dried over Na2SO4 filtered and concentrated under vacuum to give the title compound as a thick oil (34 g).
Workup
- temperatureto warm up to RT
- extractionextracted with DCM (twice)
- washThe collected organic phases were washed with a saturated solution of NaHCO3
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-4d194062fd7d472495b63db325ced758
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09321776B2
Reaction notes
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