Propanal → HCID 57112010, compound

Participants

Reaction Steps

A solution of 2-(1,3-dihydro-6-methoxy-7-methyl-3-oxo-4-p-toluenesulfonyloxy-5-isobenzofuranyl)acetaldehyde (10.0 g) and 2-triphenylphosphoranylidine propionaldehyde (10.3 g) in toluene (150 mL) was heated under nitrogen atmosphere using an oil bath at 80° C. After allowing the reaction to proceed for 16 hours, the mixture was cooled to ambient temperature and subjected to flash chromatography three times (7/2/1 hexanes/methylene chloride/methanol; 6/3/1 hexanes/methylene chloride/methanol; 1/1/1 hexanes/methylene chloride/ether). The residual solid (5.56 g) was recrystallized from ethyl acetate (200 mL) to afford 4-(1,3-dihydro-6-methoxy-7-methyl-3-oxo-4-p-toluenesulfonyloxy -5-isobenzofuranyl)2-methylbut-2-enaldehyde (2.65 g), m.p. 168.3°-173.2° C., impure with the starting aldehyde.

Provenance & Evidence