Triethylamine → Methanesulfonic acid 3-benzenesulfonyl-3-methylbutyl ester

HRID 2212070Notes

Reaction equation

HRID 2212070 reaction equation
[C:1]1([S:7]([C:10]([CH3:15])([CH3:14])[CH2:11][CH2:12][OH:13])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>>[C:1]1([S:7]([C:10]([CH3:15])([CH3:14])[CH2:11][CH2:12][O:13][S:24]([CH3:23])(=[O:26])=[O:25])(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 149069793-Benzenesulfonyl-3-methyl-butan-1-ol

Product 1

HCID 86595010Methanesulfonic acid 3-benzenesulfonyl-3-methylbutyl esterYield 103.1%

Procedure

A solution of 3-benzenesulfonyl-3-methyl-butan-1-ol (2.17 g, 9.5 mmol), triethylamine (2.0 ml, 14.25 mmol), methanesulphonyl chloride (0.9 ml, 11.78 mmol) and 4-N,N-dimethylaminopyridine (12 mg, 0.01 mmol) was stirred at 0° C. for 45 min. After quenching with satd. NaHCO3, the mixture was extracted into dichloromethane. The combined organic extracts were dried (Na2SO4) and concentrated to give the title product (3.0 g).

Workup

  1. customAfter quenching with satd
  2. extractionNaHCO3, the mixture was extracted into dichloromethane
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4f69f1bcb9d44b4b9564223aaaf7654c
Source dataset
uspto-grants-2006_09
Patent number
US07101892B2

Reaction notes

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