Potassium Hydroxide → 209746-56-5

HRID 1003934Notes

Reaction equation

HRID 1003934 reaction equation
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

Participants

8

Reactant 4

HCID 14797Potassium HydroxideHCID 27738751-Benzofuran-5-carbaldehydeHCID 70273496HCID 70273496, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 6918439209746-56-5Yield 74.4%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 178503042HCID 178503042, compoundCatalystHCID 702EthanolSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-a3f588c4174a42c3927c4179b141906a
Source dataset
uspto-grants-2000_04
Patent number
US06048842

Reaction notes

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