Dichloromethane → 2-Cyclopropylethyl methanesulfonate

HRID 41230

Reaction equation

HRID 41230 reaction equation
[CH:1]1([CH2:4][CH2:5][OH:6])[CH2:3][CH2:2]1.ClCCl.[CH3:10][S:11](Cl)(=[O:13])=[O:12].C(N(CC)CC)C>C(OCC)(=O)C.O>[CH3:10][S:11]([O:6][CH2:5][CH2:4][CH:1]1[CH2:3][CH2:2]1)(=[O:13])=[O:12]

Participants

7

Procedure

To a mixture of 2-cyclopropylethanol (5.35 g, 62.1 mmol) and dichloromethane (107 mL) were added methanesulfonyl chloride (5.29 mL, 68.3 mmol) and triethylamine (13.1 mL, 93.1 mmol) in that order while stirring on ice, and the resulting mixture was stirred for 1 hour. Water and ethyl acetate were then 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 then filtered, and the solvent in the filtrate was distilled off under reduced pressure to obtain the title compound (10.3 g, 62.7 mmol).

Workup

  1. stirringthe resulting mixture was stirred for 1 hour
  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 distilled off under reduced pressure

Sources & evidence

ORD record
ord-8cc13b95ca8b4518a5dbae1952f6e897
Source dataset
uspto-grants-2013_09
Patent number
US08530504B2

Linked notes

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