Ethanol → HCID 58424985, compound
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)[C:6]([OH:8])=[O:7].S(Cl)(Cl)=O.[CH2:19](O)[CH3:20]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)[C:6]([O:8][CH2:19][CH3:20])=[O:7]Participants
4
Procedure
The compound (5.33 g, 27.0 mmol) prepared in step 1 was dissolved in absolute ethanol (55.0 ml), added dropwise with thionyl chloride (2.96 ml, 40.55 mmol) at 0° C. The resulting mixture was refluxed for 6 hours. After completion, the reaction mixture was concentrated under reduced pressure and mixed with sodium bicarbonate aqueous solution. The mixture was extracted with dichloromethan, dried over anhydrous magnesium sulfate, and concentrated to dryness. The residue was then purified by flash column chromatography (dichloromethane:hexane=4:1) to obtain the title compound (5.1 g, yield: 85.6%, ivory solid).