Triethylamine → 2-Butene-1,4-diol, 1,4-dimethanesulfonate, (2Z)-

HRID 2216353Notes

Reaction equation

HRID 2216353 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

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 6437902-Butene-1,4-diol, (2Z)-

Product 1

HCID 64333312-Butene-1,4-diol, 1,4-dimethanesulfonate, (2Z)-

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

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

  1. customThen, the insoluble matters were removed by filtration
  2. filtrationThe filtrate was further filtered through silica gel
  3. washwashed with ethyl acetate
  4. 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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