Ammonium formate → T-1095

HRID 1003937노트

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HRID 1003937 반응식
[O:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[C:7]([CH2:10][CH2:11][C:12]([C:14]3[C:19]([O:20]CC=C)=[CH:18][C:17]([CH3:24])=[CH:16][C:15]=3[O:25][C@@H:26]3[O:34][C@H:33]([CH2:35][O:36][C:37]([O:39][CH3:40])=[O:38])[C@@H:31]([OH:32])[C@H:29]([OH:30])[C@H:27]3[OH:28])=[O:13])[CH:8]=[CH:9][C:2]1=2.C([O-])=O.[NH4+]>C(#N)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[O:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[C:7]([CH2:10][CH2:11][C:12]([C:14]3[C:19]([OH:20])=[CH:18][C:17]([CH3:24])=[CH:16][C:15]=3[O:25][C@@H:26]3[O:34][C@H:33]([CH2:35][O:36][C:37]([O:39][CH3:40])=[O:38])[C@@H:31]([OH:32])[C@H:29]([OH:30])[C@H:27]3[OH:28])=[O:13])[CH:8]=[CH:9][C:2]1=2

참가 물질

5

반응물 2

HCID 2723923Ammonium formateHCID 21967943HCID 21967943, 화합물

생성물 1

HCID 6918410T-1095수율 84.8%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 6342Acetonitrile용매

실험 절차

3-(5-Benzo[b]furanyl)-2'-(6-O-methoxycarbonyl-β-D-glucopyranosyloxy)-6'-allyloxy-4'-methylpropiophenone (470 mg) is dissolved in acetonitrile (7 ml), and thereto are added dichlorobis(triphenylphosphine)-palladium (II) (17.7 mg,) and ammonium formate (319 mg), and the mixture is heated under reflux overnight. After cooling, the insoluble materials are removed by filtration, and the filtrate is concentrated. To the residue are added ethyl acetate and water, and the mixture is shaken. The organic layer is separated, washed with water, dried, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (solvent; chloroform/methanol) to give 3-(5-benzo[b]furanyl)-2'-(6-O-methoxycarbonyl-β-D-glucopyranosyloxy)-6'-hydroxy-4'-methylpropiophenone (370 mg).

후처리

  1. temperaturethe mixture is heated
  2. temperatureunder reflux overnight
  3. temperatureAfter cooling
  4. customthe insoluble materials are removed by filtration
  5. concentrationthe filtrate is concentrated
  6. additionTo the residue are added ethyl acetate and water
  7. customThe organic layer is separated
  8. washwashed with water
  9. customdried
  10. concentrationconcentrated under reduced pressure
  11. customThe residue is purified by silica gel column chromatography (solvent; chloroform/methanol)

출처 및 근거

ORD 기록
ord-8e587278fae74a85b742becb3303a20c
출처 데이터셋
uspto-grants-2000_04
특허 번호
US06048842

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