HCID 54184183, compound → HCID 53931433, compound

HRID 261539Notes

Reaction equation

HRID 261539 reaction equation
[CH3:1][O:2][C:3](=[O:19])[C:4](=O)[C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[Cl:14])[CH2:10][C:9]([CH2:16][CH3:17])([CH3:15])[CH2:8]2.[H][H]>CO.S(=O)(=O)(O)O.[Pt](=O)=O>[CH3:1][O:2][C:3](=[O:19])[CH2:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[Cl:14])[CH2:10][C:9]([CH2:16][CH3:17])([CH3:15])[CH2:8]2

Participants

6

Reactant 2

HCID 54184183HCID 54184183, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 53931433HCID 53931433, compound

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 887MethanolSolventHCID 1118Sulfuric AcidSolvent

Procedure

A solution of 5.2 g of 2-ethyl-6-chloro-2-methyl-α-oxo-5-indanacetic acid methyl ester in 100 cc of methanol and 10 cc of concentrated sulphuric acid is hydrogenated at 45° and a hydrogen pressure of 5 atmospheres with the addition of 1.0 g of platinum(IV) oxide. After the take up of the theoretic amount of hydrogen the catalyst is filtered off, the solution is diluted with a 5% sodium bicarbonate solution and extracted with ether. The extract is washed with water, dried over sodium sulphate and concentrated by evaporation. The resulting title compound is purified by chromatography. Thin layer chromatogram: Rf value 0.60 (adsorbent: silica gel, eluant: chloroform).

Workup

  1. customis hydrogenated at 45°
  2. filtrationAfter the take up of the theoretic amount of hydrogen the catalyst is filtered off
  3. additionthe solution is diluted with a 5% sodium bicarbonate solution
  4. extractionextracted with ether
  5. washThe extract is washed with water
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated by evaporation
  8. customThe resulting title compound is purified by chromatography

Sources & evidence

ORD record
ord-3c680a05fcd44f4d8351be645d3fcffd
Source dataset
uspto-grants-1979_08
Patent number
US04166131

Reaction notes

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