Cesium carbonate → HCID 57707034, compound

HRID 1662408Notes

Reaction equation

HRID 1662408 reaction equation
[CH3:1][C:2]1([CH3:25])[CH2:6][CH2:5][CH2:4][CH:3]1[C:7]1[CH:12]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[CH:10]=[CH:9][C:8]=1[C:17]1[CH:22]=[C:21]([OH:23])[CH:20]=[CH:19][C:18]=1[F:24].C(=O)([O-])[O-].[Cs+].[Cs+].[F:32][C:33]([F:37])([F:36])[CH2:34]I>CN(C=O)C.O>[CH3:1][C:2]1([CH3:25])[CH2:6][CH2:5][CH2:4][CH:3]1[C:7]1[CH:12]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[CH:10]=[CH:9][C:8]=1[C:17]1[CH:22]=[C:21]([O:23][CH2:34][C:33]([F:37])([F:36])[F:32])[CH:20]=[CH:19][C:18]=1[F:24]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 677091,1,1-Trifluoro-2-iodoethaneHCID 57706198HCID 57706198, compound

Product 1

HCID 57707034HCID 57707034, compoundYield 91.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a flask containing 66.23A (0.100 g, 0.29 mmol) and cesium carbonate (0.29 g, 0.88 mmol) in DMF (2 mL) was added 1,1,1-trifluoro-2-iodoethane (0.12 g, 0.58 mmol) (commercially available from Aldrich), and stirring was continued for 5 hours. The reaction was diluted with water and extracted three times with EtOAc. After drying over anhydrous magnesium sulfate and filtering, the organic solvent was removed under reduced pressure and the product was then purified on silica gel (0-10% EtOAc in hexanes) to yield 66.23B as a colorless oil (0.113 g, 91% yield).

Workup

  1. extractionextracted three times with EtOAc
  2. dry with materialAfter drying over anhydrous magnesium sulfate
  3. filtrationfiltering
  4. customthe organic solvent was removed under reduced pressure
  5. customthe product was then purified on silica gel (0-10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-c7f5279b33cf44b4ada8b4308b821ae5
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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