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

HRID 886694Notes

Reaction equation

HRID 886694 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 84.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3,3,3-Trifluoro-2-hydroxy-2-({[(4-methylphenyl) sulfonyl]oxy}methyl)propyl 4-methylbenzenesulfonate (14.29 g, 29 mmol) in dichloromethane (75 ml) was pumped through a cartridge containing PS-carbonate resin (not pre-swelled) (3 mmol/g, 25 g, 75 mmol) at 675 microliters/min. The temperature was set to approx. 50° C. by wrapping a Whatman thin film heater around the cartridge. The pressure was regulated at 40 psi. After all the reagent had been aspirated, the column was washed through with dichloromethane—at this point the column started to leak slightly and the back pressure regulator had to be removed to reduce the pressure. The collected solution was concentrated in vacuo to afford the title compound (7.25 g).

Workup

  1. customwas set to approx. 50° C.
  2. washthe column was washed through with dichloromethane—at this point the column
  3. customto be removed
  4. concentrationThe collected solution was concentrated in vacuo

Sources & evidence

ORD record
ord-8c1a3dd5959f457f892f5fcac414936d
Source dataset
uspto-grants-2012_08
Patent number
US08247377B2

Reaction notes

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