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

HRID 1372902
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HRID 1372902 반응식
[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
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참가 물질

6

반응물 4

HCID 297MethaneHCID 24007Selenium DioxideHCID 312751,4-DioxaneHCID 21072863HCID 21072863, 화합물

생성물 1

HCID 210728546-benzyloxy-8-(2-ethoxy-2-hydroxy-acetyl)-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one

시약·촉매·용매 1

HCID 962Water용매

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온도
-18 °C

실험 절차

50.12 g (154 mmol) 8-acetyl-6-benzyloxy-2,2-dimethyl-benzo[1,4]oxazin-3-one are reacted with selenium dioxide as oxidising 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 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 recrystallisation from ethanol the product is obtained in the form of a beige solid. Yield: 8.95 g (15%).

후처리

  1. temperatureAfter cooling
  2. filtrationthe solid is filtered off
  3. washwashed with dioxane
  4. customThe filtrate is evaporated down
  5. dissolutionthe residue is dissolved in 550 mL ethanol
  6. temperaturerefluxed for 30 minutes
  7. filtrationIt is filtered
  8. customis precipitated which
  9. filtrationfiltered
  10. customAfter recrystallisation from ethanol the product
  11. customis obtained in the form of a beige solid

출처 및 근거

ORD 기록
ord-29c15422cf4047f4be2ba901555b263e
출처 데이터셋
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07160882B2

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