HCID 10245979, compound → HCID 54397933, compound

HRID 375002Notes

Reaction equation

HRID 375002 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]([Cl: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)C.[Pt]=O>[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]([Cl:22])[CH:20]=[CH:21][C:9]=2[O:8][C:7]1=[O:23])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 10245979HCID 10245979, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 54397933HCID 54397933, compoundYield 50.6%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

To a solution of 6-chloro-2-oxo-4-phenyl-2H-1-benzopyran-3-carboxylic acid ethyl ester (4.4 g) in ethanol (300 ml) was added platinum oxide (0.30 g), followed by stirring at room temperature in a hydrogen atmosphere (3 to 4 atm) for 3 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 6-chloro-3,4-dihydro-2-oxo-4-phenyl-2H-1-benzopyran-3-carboxylic acid ethyl ester as colorless crystals (2.24 g).

Workup

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

Sources & evidence

ORD record
ord-13f82280c7534135a335b2a7f1cd4c36
Source dataset
uspto-grants-1996_01
Patent number
US05482967

Reaction notes

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