Allyl chloroformate → HCID 86607070, compound

Participants

Reaction Steps

A mixture of ethyl (4-acetyl-2-aminophenyl)acetate and ethyl [2-amino-4-(1-hydroxyethyl)phenyl]acetate (20.4 g) prepared by step d) was dissolved in pyridine (184 mL) and thereto was dropped at room temperature allyloxycarbonyl chloride (22.2 g), followed by stirring for 30 minutes. To the reaction mixture were added a saturated ammonium chloride solution (100 mL) and saturated brine (100 mL), and then pyridine was removed in vacuo. To the aqueous layer was added 2M hydrochloric acid (200 mL) and the mixture was extracted with ethyl acetate (3×100 mL). The organic layers were combined, washed with 2M hydrochloric acid (3×50 mL) and saturated brine (50 mL), filtered and the solvent was removed in vacuo. The residue was purified with column chromatography (SiO2 500 g, hexane/ethyl acetate 3:1˜1:1) to give ethyl (4-acetyl-2-{[(allyloxy)carbonyl]amino}phenyl)acetate (7.34 g, 26%) as a gray oil, and ethyl [2-{[(allyloxy)carbonyl]amino}-4-(1-hydroxyethyl)phenyl]acetate (14.1 g, 50%) as a purple oil.

Provenance & Evidence