Triethylamine → Hex-5-yn-1-yl methanesulfonate
Reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH2:6]([OH:12])[CH2:7][CH2:8][CH2:9][C:10]#[CH:11].C(N(CC)CC)C>ClCCl>[CH3:1][S:2]([O:12][CH2:6][CH2:7][CH2:8][CH2:9][C:10]#[CH:11])(=[O:4])=[O:3]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of methanesulphonyl chloride (23.7 ml) in dry dichloromethane (25 ml.) was added dropwise to a solution of hex-5-yn-1-ol (Lancaster Synthesis, 25 g) and triethylamine (47.3 ml) in dichloromethane (300 ml), and stirred under a nitrogen atmosphere at -70°. The resulting mixture was allowed to warm to room temperature over 16 hours. The mixture was then washed with water, dilute hydrochloric acid, saturated sodium bicarbonate solution and brine before drying over anhydrous magnesium sulphate and evaporation in vacuo. Hex-5-ynyl methanesulphonate was obtained as an oil (43.6 g) and was used without purification.
Workup
- washThe mixture was then washed with water, dilute hydrochloric acid, saturated sodium bicarbonate solution and brine
- dry with materialbefore drying over anhydrous magnesium sulphate and evaporation in vacuo
Sources & evidence
- ORD record
- ord-7415742719244aa4b909c6f45982eb3c
- Source dataset
- uspto-grants-1991_06
- Patent number
- US05026874
Reaction notes
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