Ethylene Glycol → tert-butyl 9-(2-methyl-3-furyl)-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of tert-butyl 9-(2-formyl-3-furyl)-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (750 mg, 2.18 mmol), hydrazine monohydrate (0.300 ml, 6.18 mmol), ethylene glycol (15 ml) and methanol (5 ml) was stirred at 85° C. for 10 min. After cooling to room temperature, potassium hydroxide (500 mg, 8.91 mmol) was added, and the mixture was stirred at 100° C. for 0.5 hr. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to give the desired product (300 mg, 41.8%) as an oil.

Provenance & Evidence