2-Piperidone → 6-pentafluoroethyl-2,2-bisfluoromethyl-4-(2-oxo-1-piperidinyl)-2H-1-benzopyran

HRID 977608Notes

Reaction equation

HRID 977608 reaction equation
O1[CH:7]2[CH:2]1[C:3]([CH2:21][F:22])([CH2:19][F:20])[O:4][C:5]1[CH:11]=[CH:10][C:9]([C:12]([F:18])([F:17])[C:13]([F:16])([F:15])[F:14])=[CH:8][C:6]=12.[NH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][C:24]1=[O:29].CC(C)([O-])C.[K+]>O1CCCC1>[F:18][C:12]([F:17])([C:9]1[CH:10]=[CH:11][C:5]2[O:4][C:3]([CH2:21][F:22])([CH2:19][F:20])[CH:2]=[C:7]([N:23]3[CH2:28][CH2:27][CH2:26][CH2:25][C:24]3=[O:29])[C:6]=2[CH:8]=1)[C:13]([F:14])([F:15])[F:16]

Participants

5

Reactant 3

HCID 126652-PiperidoneHCID 158717923,4-epoxy-6-pentafluoroethyl-2,2-bisfluoromethyl-3,4-dihydro-2H-1-benzopyranHCID 23665647Potassium tert-butoxide

Product 1

HCID 158410086-pentafluoroethyl-2,2-bisfluoromethyl-4-(2-oxo-1-piperidinyl)-2H-1-benzopyranYield 3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 0.54 g of 3,4-epoxy-6-pentafluoroethyl-2,2-bisfluoromethyl-3,4-dihydro-2H-1-benzopyran, 0.24 g of 2-piperidinone and 10 ml of tetrahydrofuran was added 0.27 g of potassium tert-butoxide with stirring under ice-cooling. The mixture was stirred for 6 hours under ice-cooling and then stirred at room temperature for 16 hours. Ice water was added to the mixture, which was then extracted with methylene chloride. After the organic layer was washed with water and dried, the solvent was distilled off. The resultant residue was purified using silica gel column chromatography (developing solution, MeOH:CH2Cl2 =1:99) to obtain from the first eluted fraction 0.02 g of 6-pentafluoroethyl-2,2-bisfluoromethyl-4-(2-oxo-1-piperidinyl)-2H-1-benzopyran represented by the following formula having a melting point of 149°-150° C.

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred for 6 hours under ice-
  3. temperaturecooling
  4. stirringstirred at room temperature for 16 hours
  5. extractionwas then extracted with methylene chloride
  6. washAfter the organic layer was washed with water
  7. customdried
  8. distillationthe solvent was distilled off
  9. customThe resultant residue was purified

Sources & evidence

ORD record
ord-cc2cbbf097014033a33ad222f687fd4b
Source dataset
uspto-grants-1997_03
Patent number
US05614633

Reaction notes

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