Methane → 6-benzyloxy-8-(2-ethoxy-2-hydroxy-acetyl)-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one

HRID 2223111Notes

Reaction equation

[C:1]([C:4]1[C:13]2[O:12][C:11]([CH3:15])([CH3:14])[C:10](=[O:16])[NH:9][C:8]=2[CH:7]=[C:6]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:5]=1)(=[O:3])[CH3:2].[Se](=O)=[O:26].C.[O:29]1CCO[CH2:31][CH2:30]1>O>[CH2:18]([O:17][C:6]1[CH:5]=[C:4]([C:1](=[O:3])[CH:2]([O:29][CH2:30][CH3:31])[OH:26])[C:13]2[O:12][C:11]([CH3:15])([CH3:14])[C:10](=[O:16])[NH:9][C:8]=2[CH:7]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

Conditions

Temperature: -18 °C

Procedure

50.12 g (154 mmol) is 8-acetyl-6-benzyloxy-2,2-dimethylbenzo[1,4]oxazin-3-one is reacted with selenium dioxide as oxidizing agent and activated charcoal in refluxing dioxane and some water. After cooling, the solid is filtered off and washed with dioxane. The filtrate is evaporated down and the residue is dissolved in 550 mL of ethanol and refluxed for 30 minutes. It is filtered and the mother liquor is cooled to −18° C., during which time a solid is precipitated which is suction filtered. After recrystallization from ethanol, the product is obtained in the form of a beige solid. Yield: 8.95 g (15%).

Workup

temperatureAfter cooling
filtrationthe solid is filtered off
washwashed with dioxane
customThe filtrate is evaporated down
dissolutionthe residue is dissolved in 550 mL of ethanol
temperaturerefluxed for 30 minutes
filtrationIt is filtered
customis precipitated which
filtrationfiltered
customAfter recrystallization from ethanol
customthe product is obtained in the form of a beige solid

Sources & evidence

ORD record: ord-d6b6dd29ebcb4be697a1aa306d61591c
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07375104B2

Reaction notes

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