HCID 60135721, compound → HCID 60135722, compound

HRID 386928Notes

Reaction equation

HRID 386928 reaction equation
C([O:8][CH2:9][C:10]([O:12][C:13]1[CH:22]=[C:21]2[C:16]([C:17](=[O:41])[C:18]([C:23]3[CH:28]=[CH:27][C:26]([O:29][C:30](=[O:40])[CH2:31][O:32]CC4C=CC=CC=4)=[CH:25][CH:24]=3)=[CH:19][O:20]2)=[CH:15][CH:14]=1)=[O:11])C1C=CC=CC=1>C(OCC)(=O)C.[Pd]>[OH:8][CH2:9][C:10]([O:12][C:13]1[CH:22]=[C:21]2[C:16]([C:17](=[O:41])[C:18]([C:23]3[CH:28]=[CH:27][C:26]([O:29][C:30](=[O:40])[CH2:31][OH:32])=[CH:25][CH:24]=3)=[CH:19][O:20]2)=[CH:15][CH:14]=1)=[O:11]

Participants

4

Reactant 1

HCID 60135721HCID 60135721, compound

Product 1

HCID 60135722HCID 60135722, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Benzyloxy-acetic acid 4-[7-(2-benzyloxy-acetoxy)-4-oxo-4H-chromen-3-yl]-phenyl ester 42 (1 gram, 1.82 mmol) is dissolved in ethyl acetate (50 ml) in a pressure vessel, Palladium on carbon (5%, 0.5 gram) added and the mixture stirred under an atmosphere of hydrogen (4 Kg) for 22 hours. The catalyst is removed by filtration, ethyl acetate distilled under vacuum. The crude 43 can be purified by column chromatography on silica gel using benzene: ethyl acetate (8:2) as eluant to get the desired product.

Workup

  1. customThe catalyst is removed by filtration, ethyl acetate
  2. distillationdistilled under vacuum
  3. customThe crude 43 can be purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-4d7e3a0b8c834dbd81de8191b16a3c24
Source dataset
uspto-grants-2013_02
Patent number
US08372882B2

Reaction notes

Loading…