Water → Cyclopropanemethanol, 2,2-difluoro-, 1-methanesulfonate

HRID 1026326Notes

Reaction equation

HRID 1026326 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[F:6][C:7]1([F:12])[CH2:9][CH:8]1[CH2:10][OH:11].C(N(CC)CC)C.O>C1COCC1>[CH3:1][S:2]([O:11][CH2:10][CH:8]1[CH2:9][C:7]1([F:12])[F:6])(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 2761401(2,2-Difluorocyclopropyl)methanol

Product 1

HCID 58198163Cyclopropanemethanol, 2,2-difluoro-, 1-methanesulfonate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methanesulfonyl chloride (1.43 mL) was added to a solution of (2,2-difluorocyclopropyl)methanol (1.00 g) and triethylamine (2.58 mL) in THF (10 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 in vacuo. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (1.47 g) as a colorless 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 in vacuo
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-8b19d6c282684771ab89f3e86b77613a
Source dataset
uspto-grants-2014_05
Patent number
US08729102B2

Reaction notes

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