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

HRID 551421Notes

Reaction equation

HRID 551421 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-methylphenyl) 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 Fluke, 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-63dea82ec74341deac3639a8e6f5aba2
Source dataset
uspto-grants-2011_05
Patent number
US07947727B2

Reaction notes

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