Trifluoromethanesulfonic anhydride → HCID 22138897, compound

HRID 2041437Notes

Reaction equation

HRID 2041437 reaction equation
S([O:8][S:9]([C:12]([F:15])([F:14])[F:13])(=[O:11])=[O:10])(C(F)(F)F)(=O)=O.[F:16][C:17]([F:26])([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:18]O.C(C1C=C(C)C=C(C(C)(C)C)N=1)(C)(C)C>ClCCl.CCCCC>[F:15][C:12]([F:13])([F:14])[S:9]([O:8][CH2:18][C:17]([F:26])([F:16])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)(=[O:10])=[O:11]

Participants

6

Reactant 3

HCID 67749Trifluoromethanesulfonic anhydrideHCID 988982,6-Di-tert-butyl-4-methylpyridineHCID 97938912,2-Difluoro-2-phenylethanol

Product 1

HCID 22138897HCID 22138897, compoundYield 64.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8003PentaneSolvent

Procedure

Add triflic anhydride (1.28 mL, 2.14 g) dropwise to a stirred solution of 2,2-difluoro-2-phenyl-ethanol (0.8 g, 5.06 mmol) and 2,6-di-tert-butyl-4-methylpyridine (1.556 g, 7.59 mmol) in anhydrous dichloromethane (25 mL) at −78° C. Stir the reaction overnight while the temperature warms up. Dilute the mixture with pentane and filter the precipitate over Celite®. Concentrate the filtrate in vacuo and purify the crude mixture by chromatography on silica gel eluting with hexane and hexane/EtOAc (95:5) to provide the title compound (946 mg, 64%).

Workup

  1. customthe reaction overnight while the temperature
  2. filtrationfilter the precipitate over Celite®
  3. concentrationConcentrate the filtrate in vacuo
  4. custompurify the crude mixture by chromatography on silica gel eluting with hexane and hexane/EtOAc (95:5)

Sources & evidence

ORD record
ord-a8eeaf2fe74a48d6b11cbcfdbbe523ba
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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