HCID 19874534, compound → HCID 19874542, compound

HRID 465467Notes

Reaction equation

HRID 465467 reaction equation
[CH2:1]([C:5]1[CH:21]=[CH:20][C:8]([O:9][CH2:10][C:11]2[O:15][C:14]([C:16]([O:18][CH3:19])=[O:17])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)[C:2]([CH3:4])=[O:3]>CO.[Rh]>[CH2:1]([C:5]1[CH:21]=[CH:20][C:8]([O:9][CH2:10][CH:11]2[O:15][CH:14]([C:16]([O:18][CH3:19])=[O:17])[CH2:13][CH2:12]2)=[CH:7][CH:6]=1)[C:2]([CH3:4])=[O:3]

Participants

4

Reactant 1

HCID 19874534HCID 19874534, compound

Product 1

HCID 19874542HCID 19874542, compound

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 887MethanolSolvent

Procedure

Methyl 5-[4-acetonylphenoxymethyl]furan-2-carboxylate, ethylene ketal (12.5 g) was hydrogenated at ambient temperature and pressure, in methanol, in the presence of 5% rhodium on alumina. The reaction mixture was filtered and evaporated to an oil which was purified by column chromatography on silica gel. Elution with chloroform gave methyl 5-[4-acetonylphenoxymethyl]tetrahydrofuran-2-carboxylate, ethylene ketal.

Workup

  1. customwas hydrogenated at ambient temperature
  2. filtrationThe reaction mixture was filtered
  3. customevaporated to an oil which
  4. customwas purified by column chromatography on silica gel
  5. washElution with chloroform

Sources & evidence

ORD record
ord-529b70bbe77b412c929004880d4de797
Source dataset
uspto-grants-1992_10
Patent number
US05153210

Reaction notes

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