Dichloromethane → 2-Methoxyethyl methanesulfonate

HRID 1295708Notes

Reaction equation

HRID 1295708 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH3:6][O:7][CH2:8][CH2:9][OH:10].C(N(CC)CC)C.ClCCl>O>[CH3:6][O:7][CH2:8][CH2:9][O:10][S:2]([CH3:1])(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 80192-MethoxyethanolHCID 8471TriethylamineHCID 31297Methanesulfonyl chloride

Product 1

HCID 1462932-Methoxyethyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methanesulfonyl chloride (15 g, 0.13 mol) was added to a mixture of 2-methoxy ethanol (10 g, 0.13 mol), triethylamine (26.5 g, 0.26 mol) and dichloromethane (150 g) at 0° C. After being stirred at room temperature overnight, water (100 g) was added to the reaction mixture. The layers were separated and the organic layer was concentrated in vacuo at room temperature. This gave 13.1 g (65%) of the title mesylate as an oil. 1H NMR analysis supports the stated structure. *Previously reported in Tetrahedron 1995, 51, 4867-4890.

Workup

  1. customThe layers were separated
  2. concentrationthe organic layer was concentrated in vacuo at room temperature

Sources & evidence

ORD record
ord-5b6a18b538ce40ac9b7e3e2dea2c6f57
Source dataset
uspto-grants-2007_07
Patent number
US07244722B2

Reaction notes

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