Tetrahydrofuran → (5-Chloropyridin-2-yl)methyl methanesulfonate

HRID 15072

Reaction equation

HRID 15072 reaction equation
C(N(CC)CC)C.[CH3:8][S:9](Cl)(=[O:11])=[O:10].O1CCCC1.[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([CH2:25][OH:26])=[N:23][CH:24]=1>O>[CH3:8][S:9]([O:26][CH2:25][C:22]1[CH:21]=[CH:20][C:19]([Cl:18])=[CH:24][N:23]=1)(=[O:11])=[O:10]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 20537893(5-Chloropyridin-2-yl)methanol

Product 1

HCID 70700476(5-Chloropyridin-2-yl)methyl methanesulfonateYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Triethylamine (12 mL) and methanesulfonyl chloride (5.7 mL) were added to tetrahydrofuran (150 mL) solution of 5-chloro-2-hydroxymethylpyridine (12.77 g) under cooling with ice, and stirred for 30 minutes under cooling with ice. After addition of water (150 mL), the reaction liquid was extracted with ethyl acetate (150 mL+150 mL), and the organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. Concentrating the solvent under reduced pressure, the residue was crystallized from ethyl acetate-diisopropyl ether mixed solvent to provide the title compound (14.65 g, 99%).

Workup

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice
  3. customthe reaction liquid
  4. extractionwas extracted with ethyl acetate (150 mL+150 mL)
  5. washthe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationConcentrating the solvent under reduced pressure
  8. customthe residue was crystallized from ethyl acetate-diisopropyl ether mixed solvent

Sources & evidence

ORD record
ord-9a5fbfe159bf429d946f028309c04113
Source dataset
uspto-grants-2010_06
Patent number
US07732456B2

Linked notes

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