Potassium Hydroxide → T-1095A

HRID 1003934노트

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HRID 1003934 반응식
C([C@@:4]1([OH:35])[C@@:9](C(=O)C)([OH:10])[C@:8](C(=O)C)([OH:14])[C@@H:7]([CH:18](C(=O)C)[OH:19])[O:6][C@H:5]1[O:23][C:24]1[CH:29]=[C:28]([CH3:30])[CH:27]=[C:26]([OH:31])[C:25]=1[C:32](=[O:34])[CH3:33])(=O)C.[OH-].[K+].[CH:38]([C:40]1[CH:48]=[CH:47][C:43]2[O:44][CH:45]=[CH:46][C:42]=2[CH:41]=1)=O.[H][H]>C(O)C.CN(C)C1C=CN=CC=1.[Pt].[C]>[O:44]1[CH:45]=[CH:46][C:42]2[CH:41]=[C:40]([CH2:38][CH2:33][C:32]([C:25]3[C:26]([OH:31])=[CH:27][C:28]([CH3:30])=[CH:29][C:24]=3[O:23][C@@H:5]3[O:6][C@H:7]([CH2:18][OH:19])[C@@H:8]([OH:14])[C@H:9]([OH:10])[C@H:4]3[OH:35])=[O:34])[CH:48]=[CH:47][C:43]1=2

참가 물질

8

반응물 4

HCID 14797Potassium HydroxideHCID 27738751-Benzofuran-5-carbaldehydeHCID 70273496HCID 70273496, 화합물HCID 178418361HCID 178418361, 화합물

생성물 1

HCID 6918439T-1095A수율 74.4%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 178503042HCID 178503042, 화합물촉매HCID 702Ethanol용매

실험 절차

2'-(2,3,4,6-Tetra-acetyl-β-D-glucopyranosyloxy)-6'-hydroxy-4'-methylacetophenone (120 g) is dissolved in a chilled mixture of ethanol (1.2 l) and 50% aqueous potassium hydroxide solution (240 g), and thereto is added 5-formylbenzo[b]furan (42.4 g), and the mixture is stirred at room temperature overnight under argon atmosphere. To the reaction solution are added 4-dimethylaminopyridine (29.5 g) and 10% platinum-carbon (23.58 g), and the mixture is stirred at room temperature for 4.5 hours under atmospheric pressure of hydrogen gas. The catalyst is removed by filtration, and the filtrate is washed with toluene, and acidified with 18% hydrochloric acid under ice-cooling. The mixture is extracted with ethyl acetate, and the organic layer is washed successively with water, a saturated aqueous sodium hydrogen carbonate solution, and a saturated aqueous sodium chloride solution. The washed aqueous layer is extracted with ethyl acetate, and the organic layers are combined, dried, and concentrated under reduced pressure. The residue is crystallized from water-ethanol to give 3-(5-benzo[b]furanyl)-2'-(β-D-glucopyranosyloxy)-6'-hydroxy-4'-methylpropiophenone (82.4 g).

후처리

  1. customThe catalyst is removed by filtration
  2. washthe filtrate is washed with toluene
  3. temperaturecooling
  4. extractionThe mixture is extracted with ethyl acetate
  5. washthe organic layer is washed successively with water
  6. extractionThe washed aqueous layer is extracted with ethyl acetate
  7. customdried
  8. concentrationconcentrated under reduced pressure
  9. customThe residue is crystallized from water-ethanol

출처 및 근거

ORD 기록
ord-a3f588c4174a42c3927c4179b141906a
출처 데이터셋
uspto-grants-2000_04
특허 번호
US06048842

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