HCID 53696980, compound → HCID 53861957, compound

HRID 2225721Notes

Reaction equation

HRID 2225721 reaction equation
[CH3:1][O:2][C:3](=[O:34])[C:4](=[O:33])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][O:14][C:15]2[C:24]([O:25]CC3C=CC=CC=3)=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=2)=[CH:7][CH:6]=1.[H][H]>O1CCCC1.[Pd]>[CH3:1][O:2][C:3](=[O:34])[C:4](=[O:33])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][O:14][C:15]2[C:24]([OH:25])=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=2)=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 53696980HCID 53696980, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 53861957HCID 53861957, compoundYield 18.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of alpha-oxo-4-[[2-[3-(phenylmethoxy)-2-naphthalenyloxy]ethyl]oxy]benzeneacetic acid methyl ester (0.456 g) in tetrahydrofuran (3 mL) was added to a flask containing 10% palladium on carbon catalyst and 5 mL of tetrahydrofuran in a hydrogen atmosphere. The mixture was stirred until one equivalent of hydrogen was absorbed and the reaction was filtered and the organic solvent was removed by evaporation. Chromatography on silica gel and elution with dichloromethane-hexane mixtures provided purified product. Crystallization from dichloromethane-diethyl ether gave 0.067 g of pure 4-[[2-(3-hydroxy-2-naphthalenyloxy)ethyl]oxy]-alphaoxobenzeneacetic acid methyl ester as a colorless solid, mp 177°-178° C.

Workup

  1. additionwas added to a flask
  2. customwas absorbed
  3. filtrationthe reaction was filtered
  4. customthe organic solvent was removed by evaporation
  5. washChromatography on silica gel and elution with dichloromethane-hexane
  6. custommixtures provided
  7. custompurified product
  8. customCrystallization from dichloromethane-diethyl ether

Sources & evidence

ORD record
ord-7a6dc5aeebdc499fb12d8a271ca70712
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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