5-Hydroxy-2-(4-methyl-3-pentenyl)-5-(2-trimethylsilyl-4-furyl)-2-pentenal → 3,6-Dihydro-6-hydroxy-5-(4-methyl-3-pentenyl)-2-(2-trimethylsilyl-4-furyl)-2H-pyran

Participants

Reaction Steps

5-Hydroxy-2-(4-methyl-3-pentenyl)-5-(2-trimethylsilyl-4-furyl)-2-pentenal (0.88 g, 0.274 mmol) was dissolved in 27 ml anhydrous benzene, placed in a quartz tube and deoxygenated by saturating with oxygen-free nitrogen for one hour. The solution was irradiated at 254 nm for three hours, cooled and concentrated to give a brown-yellow gum. This material was purified by flash chromatography (silica, 15 to 30% ethyl acetate/hexane). First eluted was the desired acetal followed by starting aldehyde.

Provenance & Evidence