Thionyl Chloride → HCID 69055162, compound

Participants

Reaction Steps

To a stirred solution of 6-(methoxymethoxy)-5,7,8-trimethyl-4-oxo-3,4-dihydrospiro[chromene-2,1′-cyclobutane]-3-carbaldehyde (2.0 g) in 20 mL of dichloromethane was added dropwise 5 mL of SOCl2. The reaction was allowed to stir at room temperature for 2 hr. After the reaction was complete, the mixture was concentrated and the residue was purified by flash chromatography eluted with 10-20% ethyl acetate in hexane to give 1.46 g of 3-(chloromethylene)-6-hydroxy-5,7,8-trimethylspiro[chromene-2,1′-cyclobutan]-4(3H)-one, as a yellow solid. It is a mixture of two isomers with a ratio of about 3:1, as indicated by TLC analysis.

Provenance & Evidence