Hexanal → HCID 68501164, compound

Participants

Reaction Steps

A 10 ml schlenk tube was charged with copper (I) bromide (3.6 mg, 0.025 mmol), (R,Rax)-[4-(2-diphenylphosphanyl-naphthalen-1-yl)-phthalazin-1-yl]-(1-phenylethyl)amine (15.7 mg, 0.028 mmol) and 4 Å molecular sieves (powdered, 0.25 g) and then purged with argon for 5 min. Dichloromethane (1 ml) was added and the resulting suspension was stirred for 60 min. To the reaction mixture were added triethylamine (56 mg, 0.55 mmol), 4-piperidone monohydrochloride monohydrate (powder, 154 mg, 1.0 mmol), (trimethylsilyl)acetylene (98 mg, 1.00 mmol) and n-hexanal (50 mg, 0.50 mmol). The flask was rinsed with an additional 1 ml of dichloromethane and then sealed. The reaction mixture was stirred vigorously at 23° C. for 22 hrs. The reaction mixture was directly purified by flash chromatography on silica gel (hexane/EtOAc=9:1) to give 102 mg of the title compound as a colorless oil. (Yield: 73%)

Provenance & Evidence