1,5-Diazabicyclo(4.3.0)non-5-ene → HCID 53911394, compound

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Reaction Steps

The product of step (ii) (22.8 g). 3-bromobenzaldehyde (4.5 ml) and 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) (5.95 g) in acetonitrile (50 ml) was heated under reflux for 0.5 hours. The solution was evaporated under reduced pressure. The residue was dissolved in dichloromethane, washed with 2M HCl, dried (MgSO4) and evaporated. The residue and potassium hydroxide (5.6 g) in water (100 ml) and methanol (20 ml) was heated under reflux for 8 hours. The reaction mixture was diluted with water and washed with dichloromethane. The aqueous solution was acidified to pH 1 (2N HCl) and extracted with dichloromethane. The organic solution was dried (MgSO4), evaporated and the product purified by chromatography eluting with toluene. Yield 8.5 g. Used directly in the next step.

Provenance & Evidence