Water → HCID 54432120, compound

HRID 2260657Notes

Reaction equation

HRID 2260657 reaction equation
C(OP([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])(OCC)=O)C.[H-].[Na+].[F:17][C:18]1[CH:34]=[CH:33][C:21]2[CH:22]=[CH:23][C:24]3[CH:31]=[C:30]([CH3:32])[CH:29]=[CH:28][C:25]=3[C:26](=O)[C:20]=2[CH:19]=1.O>C1COCC1.C(OCC)(=O)C>[F:17][C:18]1[CH:34]=[CH:33][C:21]2[CH:22]=[CH:23][C:24]3[CH:31]=[C:30]([CH3:32])[CH:29]=[CH:28][C:25]=3[C:26](=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:20]=2[CH:19]=1

Participants

7

Reactant 4

HCID 962WaterHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 19970865HCID 19970865, compound

Product 1

HCID 54432120HCID 54432120, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Ethyl diethylphosphonoacetate (1.3 ml) was dissolved in 30 ml of THF, and 0.26 g of sodium hydride (60% oily) was added to the solution under ice cooling, followed by stirring under the same conditions for 30 minutes. To the mixture was added dropwise 20 ml of a solution of 0.3 g of 7-fluoro-2-methyl-5-oxo-5H-dibenzo[ a,d]cycloheptene in THF, and the mixture was heated under reflux for 2 hours. After cooling, water and ethyl acetate were added to the mixture, and the organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography [eluent: hexane/ethyl acetate (10/1)] to give 0.38 g (98%) of the product as a yellow oily substance.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. temperatureAfter cooling
  4. washthe organic layer was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue was purified by silica gel column chromatography [eluent: hexane/ethyl acetate (10/1)]

Sources & evidence

ORD record
ord-30147bc3b92641ab954b328221f02527
Source dataset
uspto-grants-1995_12
Patent number
US05478840

Reaction notes

Loading…