1,5-Diazabicyclo(4.3.0)non-5-ene → HCID 14651078, compound

HRID 1199429Notes

Reaction equation

HRID 1199429 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]([CH:18]=[O:19])[C:10]([CH3:17])([CH3:16])[CH2:11][C:12]([CH3:15])([CH3:14])[CH:13]=2)=[CH:4][CH:3]=1.N12CCCC1=NCCC2>C1COCC1.C(O)C.CCOCC>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH2:13][C:12]([CH3:14])([CH3:15])[CH2:11][C:10]([CH3:17])([CH3:16])[C:9]=2[CH:18]=[O:19])=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 763491,5-Diazabicyclo(4.3.0)non-5-eneHCID 14651077HCID 14651077, compound

Product 1

HCID 14651078HCID 14651078, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

The aldehyde obtained in Step 5 (130 g, 50 mmoles) was dissolved in a solution of 50 ml of THF and 50 ml of ethanol. To this solution was added 0.62 ml (5 mmoles) of 1,5-diazabicyclo-[4,3,0]-non-5-ene and the reaction mixture stirred at room temperature for 50 hours. The reaction mixture then was diluted with ether and extracted with dilute HCl, saturated NaHCO3, and brine. The solvents were evaporated in vacuo and the residue purified by flash chromatography on silica gel.

Workup

  1. extractionextracted with dilute HCl, saturated NaHCO3, and brine
  2. customThe solvents were evaporated in vacuo
  3. customthe residue purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-e869d70fb6ac4a818c545682f4038316
Source dataset
uspto-grants-1990_02
Patent number
US04900754

Reaction notes

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