Cesium carbonate → HCID 22500955, compound

HRID 1815458Notes

Reaction equation

HRID 1815458 reaction equation
F[C:2]1[C:11]([S:12]([CH3:15])(=[O:14])=[O:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH3:16])[CH:3]=1.[F:17][C:18]1([F:23])[CH2:21][CH:20]([OH:22])[CH2:19]1.C([O-])([O-])=O.[Cs+].[Cs+]>CN1C(=O)CCC1.C([O-])(O)=O.[Na+]>[F:17][C:18]1([F:23])[CH2:21][CH:20]([O:22][C:2]2[C:11]([S:12]([CH3:15])(=[O:14])=[O:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH3:16])[CH:3]=2)[CH2:19]1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 10538364Methyl 4-fluoro-5-methanesulfonyl-2-methylbenzoateHCID 225009543,3-Difluorocyclobutanol

Product 1

HCID 22500955HCID 22500955, compoundYield 75.6%

Reagents, catalysts & solvents 2

HCID 13387N-methyl-2-pyrrolidoneSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
60 °C

Procedure

370 mg of methyl 4-fluoro-5-methanesulfonyl-2-methylbenzoate, 297 mg of 3,3-difluorocyclobutanol and 1.47 g of Cs2CO3 were dissolved in 10 ml of anhydrous NMP and stirred at 60° C. for 4 h. The reaction mixture was then diluted with 125 ml of a 50% concentrated aqueous NaHCO3 solution and extracted 3 times with 100 ml of EA each time. It was dried over Na2SO4, and the solvent was removed in vacuo. Chromatography on silica gel with DIP resulted in 380 mg of a colorless oil.

Workup

  1. extractionextracted 3 times with 100 ml of EA each time
  2. dry with materialIt was dried over Na2SO4
  3. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-f50d7cbb377e49ed9ab00b73cc6c2f55
Source dataset
uspto-grants-2005_04
Patent number
US06878748B2

Reaction notes

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