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

Temperature

70 °C

A mixture of tert-butyl 9-(5-formyl-3-furyl)-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (300 mg, 0.874 mmol), hydrazine monohydrate (0.100 ml, 2.06 mmol), ethylene glycol (6 ml) and methanol (4 ml) was stirred at 70° C. for 10 min. After cooling to room temperature, potassium hydroxide (147 mg, 2.62 mmol) was added, and the mixture was stirred at 100° C. for 1 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=2:1) to give the desired product (72.0 mg, 25.0%) as an oil.

1. temperatureAfter cooling to room temperature
2. stirringthe mixture was stirred at 100° C. for 1 hr
3. extractionthe mixture was extracted with ethyl acetate
4. washThe extract was washed with water
5. dry with materialdried over anhydrous magnesium sulfate
6. customThe solvent was evaporated under reduced pressure
7. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1)

ORD record

ord-18a83b8e4a17432fb4bf1d4c2cf26502

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08247403B2