Triethylamine → cis-1,4-Bis-(methylsulfonyloxy)-but-2-ene
Reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH2:6]([OH:11])/[CH:7]=[CH:8]\[CH2:9][OH:10].C(N(CC)CC)C>C(OCC)(=O)C>[CH3:1][S:2]([O:10][CH2:9]/[CH:8]=[CH:7]\[CH2:6][O:11][S:2]([CH3:1])(=[O:4])=[O:3])(=[O:4])=[O:3]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
In an ice bath, 26 ml of methanesulfonyl chloride was added dropwise in to a mixture of 10 g of cis-2-buten-1,4-diol, 63 ml of triethylamine and 1000 ml of ethyl acetate, followed by stirring at the same temperature for 3 hours. Then, the insoluble matters were removed by filtration. The filtrate was further filtered through silica gel and washed with ethyl acetate. Then, the filtrate was evaporated, to give 21.4 g of cis-1,4-bis(methanesulfonyloxy)-2-butene.
Workup
- customThen, the insoluble matters were removed by filtration
- filtrationThe filtrate was further filtered through silica gel
- washwashed with ethyl acetate
- customThen, the filtrate was evaporated
Sources & evidence
- ORD record
- ord-0e0d9f1eeeec46699110412446c8b6b0
- Source dataset
- uspto-grants-2006_09
- Patent number
- US07112593B2
Reaction notes
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