Water → 2-(2,2-Difluorocyclopropyl)ethyl methanesulfonate

HRID 1026330Notes

Reaction equation

HRID 1026330 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[F:6][C:7]1([F:13])[CH2:9][CH:8]1[CH2:10][CH2:11][OH:12].C(N(CC)CC)C.O>C1COCC1>[CH3:1][S:2]([O:12][CH2:11][CH2:10][CH:8]1[CH2:9][C:7]1([F:13])[F:6])(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 142797682-(2,2-Difluorocyclopropyl)ethanol

Product 1

HCID 866663152-(2,2-Difluorocyclopropyl)ethyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methanesulfonyl chloride (1.35 mL) was added to a solution of 2-(2,2-difluorocyclopropyl)ethanol (1.42 g) and triethylamine (3.24 mL) in THF (20 mL) dropwise at 0° C. The mixture was stirred at room temperature overnight. Water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (1.31 g) as a pale yellow oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-ce7c07a2af9e4a64af00e512e8907a14
Source dataset
uspto-grants-2014_05
Patent number
US08729102B2

Reaction notes

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