Diethylene Glycol Monomethyl Ether → 2-(2-Methoxyethoxy)ethyl methanesulfonate

HRID 2200573

Reaction equation

HRID 2200573 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][OH:8].[CH3:9][S:10](Cl)(=[O:12])=[O:11]>C(Cl)Cl>[CH3:9][S:10]([O:8][CH2:7][CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])(=[O:12])=[O:11]

Participants

4

Reactant 2

HCID 8134Diethylene Glycol Monomethyl EtherHCID 31297Methanesulfonyl chloride

Product 1

HCID 38156542-(2-Methoxyethoxy)ethyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(2-methoxyethoxy)ethanol (300 mg, 2.5 mmol) in DCM (5 mL) was added methanesulfonyl chloride (370 mg, 2.6 mmol) dropwise at 0° C. After stirred at this temperature for 5 min, TEA (505 mg, 5.0 mmol) was added. It was stirred at room temperature overnight. The mixture was partitioned between DCM and water. The organic layers were combined, dried over sodium sulfate, filtered and concentrated to give a crude oil product, which was used without purification. Product tlc [petroleum ether/ethyl acetate [1:1) developed with iodine, Rf 0.5]

Workup

  1. stirringIt was stirred at room temperature overnight
  2. customThe mixture was partitioned between DCM and water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a crude oil product, which
  7. customwas used without purification

Sources & evidence

ORD record
ord-e134149354544190ab9bd43f7d75f26d
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Linked notes

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