Diethyl Malonate → HCID 20373366, compound

HRID 1605621Notes

Reaction equation

HRID 1605621 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[H-].[Na+].Cl[CH:15]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[C:19]([F:27])([F:26])[C:18]([F:29])([F:28])[C:17]2[CH:30]=[CH:31][CH:32]=[CH:33][C:16]1=2>>[CH2:10]([O:9][C:1](=[O:8])[CH:2]([CH:15]1[C:16]2[CH:33]=[CH:32][CH:31]=[CH:30][C:17]=2[C:18]([F:29])([F:28])[C:19]([F:26])([F:27])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]1=2)[C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH3:11]

Participants

4

Reactant 3

HCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 20373345HCID 20373345, compound

Product 1

HCID 20373366HCID 20373366, compound

Procedure

Diethyl malonate, 90 ml., is stirred, cooled in an ice bath, and treated with 1.51 g. of 55.7% sodium hydride in mineral oil in several portions. The mixture is stirred approximately 5 minutes at room temperature and then treated with 10.03 g. (0.0334 mole) of 5-chloro-10,11-dihydro-10,10,11,11-tetrafluoro-5H-dibenzo[a,d]cycloheptene. Stirring is continued for 16 hours at approximately 40°C., 1 hour at 50°C., 1 hour at 60°C. and 1 hour at 70°C. The excess diethyl malonate is distilled at 70°-75°C. and 0.1 mm. and the residue is triturated with hexane. The insoluble mixture of product and sodium chloride is collected, washed with hexane and petroleum ether, and dried at 80°C. and 0.1 mm. The mixture is triturated with benzene and the insoluble sodium chloride is removed by filtration. Evaporation of the benzene solution under reduced pressure and recrystallization of the residual white solid from absolute ethanol affords purified product, m.p. 144° -146°C.

Workup

  1. temperaturecooled in an ice bath
  2. additiontreated with 1.51 g
  3. stirringThe mixture is stirred approximately 5 minutes at room temperature
  4. additiontreated with 10.03 g
  5. stirringStirring
  6. distillationThe excess diethyl malonate is distilled at 70°-75°C.
  7. customand the residue is triturated with hexane
  8. additionThe insoluble mixture of product and sodium chloride
  9. customis collected
  10. washwashed with hexane and petroleum ether
  11. customdried at 80°C.
  12. customThe mixture is triturated with benzene
  13. customthe insoluble sodium chloride is removed by filtration
  14. customEvaporation of the benzene solution
  15. customunder reduced pressure and recrystallization of the residual white solid from absolute ethanol
  16. customaffords
  17. custompurified product, m.p. 144° -146°C.

Sources & evidence

ORD record
ord-77b5ccea719447f191e4a6c0767215fa
Source dataset
uspto-grants-1976_04
Patent number
US03950423

Reaction notes

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