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

HRID 886914Notes

Reaction equation

[CH:1]([C:3]1[O:7][CH:6]=[C:5]([C:8]2[C:18]3[O:17][CH2:16][CH2:15][N:14]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:13][C:12]=3[CH:11]=[CH:10][CH:9]=2)[CH:4]=1)=O.O.NN.C(O)CO.[OH-].[K+]>O.CO>[CH3:1][C:3]1[O:7][CH:6]=[C:5]([C:8]2[C:18]3[O:17][CH2:16][CH2:15][N:14]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:13][C:12]=3[CH:11]=[CH:10][CH:9]=2)[CH:4]=1

Participants

Conditions

Temperature: 70 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-18a83b8e4a17432fb4bf1d4c2cf26502
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08247403B2

Reaction notes

Loading…