Carbonate Ion → (2-(Trifluoromethyl)oxiran-2-yl)methyl 4-methylbenzenesulfonate

HRID 886693Notes

Reaction equation

HRID 886693 reaction equation
CC1C=CC(S([O:11][CH2:12][C:13](O)([CH2:18][O:19][S:20]([C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=2)(=[O:22])=[O:21])[C:14]([F:17])([F:16])[F:15])(=O)=O)=CC=1.C(=O)([O-])[O-]>ClCCl>[CH3:29][C:26]1[CH:27]=[CH:28][C:23]([S:20]([O:19][CH2:18][C:13]2([C:14]([F:17])([F:16])[F:15])[CH2:12][O:11]2)(=[O:22])=[O:21])=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 19660Carbonate IonHCID 248097823,3,3-Trifluoro-2-hydroxy-2-({[(4-methylphenyl)sulfonyl]oxy}methyl)propyl 4-methylbenzenesulfonate

Product 1

HCID 24809749(2-(Trifluoromethyl)oxiran-2-yl)methyl 4-methylbenzenesulfonateYield 98.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the 3,3,3-trifluoro-2-hydroxy-2-({[(4-methyl phenyl) sulfonyl]oxy}methyl)propyl 4-methylbenzenesulfonate (186.5 g, 398.5 mmol) in dichloromethane (2500 ml) was stirred under nitrogen whilst polymer supported carbonate resin (ex Fluka, ca. 3.5 mmoles carbonate/g resin) (232 g) was added. The mixture was stirred at room temperature overnight. The resin was filtered off and the resin was washed with dichloromethane. The combined filtrate and washings were concentrated under reduced pressure to give the title compound (116.2 g) as a brown oil.

Workup

  1. additionwas added
  2. filtrationThe resin was filtered off
  3. washthe resin was washed with dichloromethane
  4. concentrationThe combined filtrate and washings were concentrated under reduced pressure

Sources & evidence

ORD record
ord-9d072531921d4a848c59b5ea5382969a
Source dataset
uspto-grants-2012_08
Patent number
US08247377B2

Reaction notes

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