Ammonium formate → T-1095

HRID 1003937Notes

Reaction equation

HRID 1003937 reaction equation
[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

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 21967943HCID 21967943, compound

Product 1

HCID 6918410T-1095Yield 84.8%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-8e587278fae74a85b742becb3303a20c
Source dataset
uspto-grants-2000_04
Patent number
US06048842

Reaction notes

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