2-(2',3'-Dimethoxyphenyl)-1-furanylethanone → 2-(2',3'-Dimethoxyphenyl)-1-tetrahydrofuranyl ethanol

HRID 233402Notes

Reaction equation

HRID 233402 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:11][C:12]([C:14]1[O:15][CH:16]=[CH:17][CH:18]=1)=[O:13].[H][H]>[Pd].CO>[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:11][CH:12]([CH:14]1[CH2:18][CH2:17][CH2:16][O:15]1)[OH:13]

Participants

5

Reactant 2

HCID 199612172-(2',3'-Dimethoxyphenyl)-1-furanylethanoneHCID 178418361HCID 178418361, compound2×

Product 1

HCID 199611152-(2',3'-Dimethoxyphenyl)-1-tetrahydrofuranyl ethanolYield 70.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 450 mg (1.8 mmol) of 2-(2',3'-dimethoxyphenyl)-1-furanylethanone, from Step 2, and 20% palladium on carbon (225 mg) in 75 mL of methanol was shaken under 4 atmospheres of hydrogen until hydrogen uptake ceased. The solution was filtered and concentrated in vacuo to give 320 mg (69% yield) of the title compound as an oily solid. This product was carried on without purification to the next step.

Workup

  1. filtrationThe solution was filtered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3bb99d86177b452e8a2630a261a78996
Source dataset
uspto-grants-1997_01
Patent number
US05591884

Reaction notes

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