2,2,3,3,3-Pentafluoropropanol → HCID 18407244, compound

HRID 1016555Notes

Reaction equation

HRID 1016555 reaction equation
F[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2.C(=O)([O-])[O-].[K+].[K+].[F:18][C:19]([F:26])([C:22]([F:25])([F:24])[F:23])[CH2:20][OH:21]>CC(N(C)C)=O>[F:18][C:19]([F:26])([C:22]([F:25])([F:24])[F:23])[CH2:20][O:21][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2

Participants

5

Reactant 3

HCID 98722,2,3,3,3-PentafluoropropanolHCID 11430Potassium CarbonateHCID 1365375-Fluoro-1-indanone

Product 1

HCID 18407244HCID 18407244, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
97.5 °C

Procedure

6.5 g of 5-fluoro-1-indanone are dissolved in 50 ml of dry dimethylacetamide and, after addition of 36.5 g of anhydrous ground potassium carbonate and 12.9 g of 2,2,3,3,3-pentafluoropropanol, stirred at 95-100° C. for 10 h. The solvent is then removed by distillation in vacuo; 300 ml of water are added to the residue, and the aqueous phase is extracted with ethyl acetate several times. The organic phase is washed with water, dried over sodium sulfate and concentrated in vacuo. Purification on silica gel affords 5-(2,2,3,3,3-pentafluoropropoxy)-1-indanone as a brown oil which crystallizes after some time; melting point 52-54° C.

Workup

  1. customThe solvent is then removed by distillation in vacuo
  2. addition300 ml of water are added to the residue
  3. extractionthe aqueous phase is extracted with ethyl acetate several times
  4. washThe organic phase is washed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customPurification on silica gel

Sources & evidence

ORD record
ord-c7d19b4151944a8b9c6c0d53b5a30c5d
Source dataset
uspto-grants-2002_11
Patent number
US06476059B1

Reaction notes

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