HCID 20255631, compound → HCID 20255662, compound

HRID 637697Notes

Reaction equation

HRID 637697 reaction equation
[CH3:1][C:2]1[C:6]2[CH:7]=[C:8]([CH3:16])[C:9]([N:11]3[CH:15]=[CH:14][CH:13]=[CH:12]3)=[CH:10][C:5]=2[O:4][CH:3]=1>[Pd].O1CCOCC1>[CH3:1][CH:2]1[C:6]2[CH:7]=[C:8]([CH3:16])[C:9]([N:11]3[CH:15]=[CH:14][CH:13]=[CH:12]3)=[CH:10][C:5]=2[O:4][CH2:3]1

Participants

4

Reactant 1

HCID 20255631HCID 20255631, compound

Product 1

HCID 20255662HCID 20255662, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 8 g (37.9 mmole) of 3,5-dimethyl-6-(pyrrol-1-yl)-benzofuran, 1.6 g of 5% palladium on carbon and 80 ml of dioxane is hydrogenated at 35° and a pressure of 4 bar. To complete the reaction, 0.8 g, each time, of 5% palladium on carbon is added a further three times during hydrogenation. After a total of 100 hours, the catalyst is filtered off and the filtrate is concentrated by evaporation in vacuo. Chromatography of the residue over silica gel (petroleum ether/methylene chloride) and distillation of the pure fractions in a bulb tube (120°/2.10-2 torr) yields 3,5-dimethyl-6-(pyrrol-1-yl)-2,3-dihydrobenzofuran in the form of a colourless oil.

Workup

  1. customis hydrogenated at 35°
  2. customthe reaction, 0.8 g
  3. filtrationAfter a total of 100 hours, the catalyst is filtered off
  4. concentrationthe filtrate is concentrated by evaporation in vacuo
  5. distillationChromatography of the residue over silica gel (petroleum ether/methylene chloride) and distillation of the pure fractions in a bulb tube (120°/2.10-2 torr)

Sources & evidence

ORD record
ord-1c29f0ab31a94d90b716a0672bc32d1a
Source dataset
uspto-grants-1985_12
Patent number
US04558043

Reaction notes

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