Benzaldehyde → HCID 86754620, compound

Participants

Reaction Conditions

Reaction Steps

0.96 g (8.6 mmol) of t-BuOK were suspended in 100 ml of dry THF under a nitrogen atmosphere, and 1.95 g (7.13 mmol) of (±)-trans-1,2,3,4,4a,5,6,7,8,8a-decahydro4a-(3-methoxyphenyl)-2-methyl-6-isoquinolinone dissolved in 50 ml of dry THF were added at -10° C. The temperature was allowed to warm to 10° C. in 1 h, then the reaction mixture was cooled to -10° C. and 0.87 ml (8.6 mmol) of benzaldehyde dissolved in 25 ml of dry THF were added. The reaction mixture was allowed to warm to room temperature and after 2 h it was poured onto H2O and extracted with AcOEt. The organic phase was dried over Na2SO4 and the solvent removed in vacuo. The residue was purified by flash chromatography, eluting with a mixture CH2Cl2 /MeOH/conc. NH4OH 94.5:5:0.5 respectively, yielding 0.85 g of the title compound.

Provenance & Evidence