Tetrahydrofuran → 6-pentafluoroethyl-2,2-bisfluoromethyl-4-(2-oxo-1-pyrrolidinyl)-2H-1-benzopyran

HRID 977607Notes

Reaction equation

HRID 977607 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[CH2:27][CH2:26][CH2:25][C:24]1=[O:28].O1CCCC1.CC(C)([O-])C.[K+]>O>[F:17][C:12]([F:18])([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[CH2:27][CH2:26][CH2:25][C:24]3=[O:28])[C:6]=2[CH:8]=1)[C:13]([F:15])([F:16])[F:14]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 120252-PyrrolidoneHCID 158717923,4-epoxy-6-pentafluoroethyl-2,2-bisfluoromethyl-3,4-dihydro-2H-1-benzopyranHCID 23665647Potassium tert-butoxide

Product 1

HCID 100463366-pentafluoroethyl-2,2-bisfluoromethyl-4-(2-oxo-1-pyrrolidinyl)-2H-1-benzopyranYield 16.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 0.41 g of 3,4-epoxy-6-pentafluoroethyl-2,2-bisfluoromethyl-3,4-dihydro-2H-1-benzopyran, 0.18 g of 2-pyrrolidinone and 8 ml of tetrahydrofuran was added 0.22 g of potassium tert-butoxide with stirring under ice-cooling and the mixture was stirred for 3.5 hours under ice-cooling and then stirred at room temperature for 4 days. Water was added and the mixture was 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 0.08 g of 6-pentafluoroethyl-2,2-bisfluoromethyl-4-(2-oxo-1-pyrrolidinyl)-2H-1-benzopyran represented by the following formula having a melting point of 104°-105° C.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 3.5 hours under ice-
  3. temperaturecooling
  4. stirringstirred at room temperature for 4 days
  5. extractionthe mixture was 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-6eb96f21878d44258c0cc6490fdacd9e
Source dataset
uspto-grants-1997_03
Patent number
US05614633

Reaction notes

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