HCID 54292911, compound → HCID 54497255, compound

HRID 1940970Notes

Reaction equation

HRID 1940970 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:23])[O:8][C:9]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][C:10]=2[C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:5])[CH3:2].[H][H]>C(O)(=O)C.[C].[Pd]>[CH2:1]([O:3][C:4]([CH:6]1[CH:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:10]2[CH:18]=[C:19]([CH3:22])[CH:20]=[CH:21][C:9]=2[O:8][C:7]1=[O:23])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 54292911HCID 54292911, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 54497255HCID 54497255, compoundYield 82.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 6-methyl-2-oxo-4-phenyl-2H-1-benzopyran-3-carboxylic acid ethyl ester (15.0 g) in acetic acid (150 ml) was added 10% palladium-carbon (3.0 g), followed by stirring at 80° C. in a hydrogen atmosphere (4 to 5 atm) for 4.5 hours. After the catalyst was filtered off, the filtrate was distilled to remove the solvent, followed by treatment of the residue with isopropyl ether, to yield 3,4-dihydro-6-methyl-2-oxo-4-phenyl-2H-1-benzopyran-3-carboxylic acid ethyl ester as colorless crystals (12.5 g).

Workup

  1. filtrationAfter the catalyst was filtered off
  2. distillationthe filtrate was distilled
  3. customto remove the solvent

Sources & evidence

ORD record
ord-239574589d324395937ef9c4fbb4d45e
Source dataset
uspto-grants-1997_12
Patent number
US05700810

Reaction notes

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