Dichloromethane → 3-Methoxybutyl methanesulfonate

HRID 41235

Reaction equation

HRID 41235 reaction equation
ClCCl.[CH3:4][O:5][CH:6]([CH3:10])[CH2:7][CH2:8][OH:9].C(N(CC)CC)C.[CH3:18][S:19](Cl)(=[O:21])=[O:20]>C(OCC)(=O)C.O>[CH3:18][S:19]([O:9][CH2:8][CH2:7][CH:6]([O:5][CH3:4])[CH3:10])(=[O:21])=[O:20]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 172913-Methoxy-1-butanolHCID 31297Methanesulfonyl chloride

Product 1

HCID 145340313-Methoxybutyl methanesulfonate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a dichloromethane (30 mL) mixture of 3-methoxy-1-butanol (3.12 g, 30.0 mmol) and triethylamine (4.62 mL, 33.0 mmol), was added methanesulfonyl chloride (4.62 mL, 33.0 mmol) while stirring on ice, and the mixture was stirred at room temperature for 30 minutes. To the mixture, were added water and ethyl acetate. After thoroughly shaking the mixture, the organic layer was separated, and the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The mixture was then filtered, and the solvent in the filtrate was then distilled off under reduced pressure.

Workup

  1. stirringthe mixture was stirred at room temperature for 30 minutes
  2. stirringAfter thoroughly shaking the mixture
  3. customthe organic layer was separated
  4. washthe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationThe mixture was then filtered
  7. distillationthe solvent in the filtrate was then distilled off under reduced pressure

Sources & evidence

ORD record
ord-e0b3177f9ddd4c4a82de19eb17756366
Source dataset
uspto-grants-2013_09
Patent number
US08530504B2

Linked notes

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