Potassium tert-butoxide → HCID 178422491, compound

HRID 279140Notes

Reaction equation

HRID 279140 reaction equation
[CH3:1][C:2]([CH3:5])([O-])[CH3:3].[K+].[NH:7]1[CH:11]=[C:10]([C:12]23CCC(=O)[CH:13]2[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=2[CH2:20]3)[N:9]=[CH:8]1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1(C)C=CC=CC=1>[CH2:1]=[C:2]1[CH:5]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[CH2:13][C:12]2([C:10]2[N:9]=[CH:8][NH:7][CH:11]=2)[CH2:20][CH2:3]1

Participants

5

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 178515456HCID 178515456, compound

Product 1

HCID 178422491HCID 178422491, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 1140TolueneSolvent

Procedure

A mixture of potassium tert-butoxide (0.38 g) and methyltriphenyl-phosphonium bromide (1.2 g) in dry toluene (20 ml) was heated at reflux for 0.5 hour. To the mixture was then added 0.55 g of 8a-(1H-imidazol-4-yl)-1,3a,8,8a-tetrahydro-2H-cyclo-penta[a]inden-3-one and the resulting mixture was heated at reflux for 4 hours. After the removal of toluene, the residue was suspended in water and extracted with methylene chloride. The combined organic layers were dried over sodium sulfate and the solvent removed under reduced pressure. The crude product was purified by flash chromatography using methylene chloride/methanol (95:5) as eluent. Recrystallization from ethyl acetate afforded 240 mg of the product, m.p. 167-174° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 0.5 hour
  3. temperaturethe resulting mixture was heated
  4. temperatureat reflux for 4 hours
  5. customAfter the removal of toluene
  6. extractionextracted with methylene chloride
  7. dry with materialThe combined organic layers were dried over sodium sulfate
  8. customthe solvent removed under reduced pressure
  9. customThe crude product was purified by flash chromatography
  10. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-048328f650c44e6e841a0aa646515aba
Source dataset
uspto-grants-2002_03
Patent number
US06362211B1

Reaction notes

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