Water → 3,3-Dimethylbutyl methanesulfonate

HRID 1049458Notes

Reaction equation

HRID 1049458 reaction equation
[CH3:1][C:2]([CH3:7])([CH3:6])[CH2:3][CH2:4][OH:5].C(N(CC)CC)C.[CH3:15][S:16](Cl)(=[O:18])=[O:17].O>C1COCC1>[CH3:15][S:16]([O:5][CH2:4][CH2:3][C:2]([CH3:7])([CH3:6])[CH3:1])(=[O:18])=[O:17]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 122333,3-Dimethyl-1-butanolHCID 31297Methanesulfonyl chloride

Product 1

HCID 190394593,3-Dimethylbutyl methanesulfonateYield 102.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3,3-dimethylbutan-1-ol (20.2 g) and triethylamine (41.3 mL) in THF (200 mL) was added methanesulfonyl chloride (24.9 g) under ice-cooling, and the mixture was stirred for 1 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (36.5 g) as a red-orange oil.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-09a3ec4136bb499badd3916476705502
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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