Dichloromethane → HCID 86626447, compound

Participants

Reaction Steps

1,1′-[(1Z,3Z)-2,3-diformylamino-1,3-butadiene-1,4-diyl]bis[methoxybenzene] (11.0 mg, 0.031 mmol) prepared in Reference Synthetic Example 4 was suspended in chloroform (200 μl) and pyridine (200 μl), and a dichloromethane solution of phosphorus oxychloride (6.4 μl, 0.069 mmol) was dropwise added under cooling with ice. After stirring for 45 minutes, the suspension was diluted with ethyl acetate, and poured into a saturated sodium hydrogen carbonate aqueous solution. Extraction with ethyl acetate was carried out twice, and the obtained organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1) to give the desired compound 1,1′-[(1Z,3Z)-2,3-diisocyano-1,3-butadiene-1,4-diyl]bis[methoxybenzene] (xanthocillin X dimethyl ether) (5.8 mg, 59%) as pale green crystals.

Provenance & Evidence