Dichloromethane → 3-Methoxypropyl methanesulfonate

HRID 41232Notes

Reaction equation

HRID 41232 reaction equation
ClCCl.[CH3:4][O:5][CH2:6][CH2:7][CH2:8][OH:9].C(N(CC)CC)C.[CH3:17][S:18](Cl)(=[O:20])=[O:19]>C(OCC)(=O)C.O>[CH3:17][S:18]([O:9][CH2:8][CH2:7][CH2:6][O:5][CH3:4])(=[O:20])=[O:19]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 741163-Methoxy-1-propanol

Product 1

HCID 116939633-Methoxypropyl methanesulfonate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a dichloromethane (50 mL) mixture of 3-methoxy-1-propanol (2.70 g, 30.0 mmol) and triethylamine (4.62 mL, 33.0 mmol), was added methanesulfonyl chloride (2.45 mL, 31.5 mmol) while stirring on ice, and the resulting mixture was stirred at room temperature for 30 minutes. Water and ethyl acetate were added to the reaction mixture. 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 filtered, and the solvent in the filtrate was then distilled off under reduced pressure.

Workup

  1. stirringthe resulting 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 filtered
  7. distillationthe solvent in the filtrate was then distilled off under reduced pressure

Sources & evidence

ORD record
ord-8552126437244a44b8826602237b613c
Source dataset
uspto-grants-2013_09
Patent number
US08530504B2

Reaction notes

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