Ethyl 4-fluoro-2,3-dihydro-7-hydroxy-1-oxo-1H-indene-2-carboxylate → HCID 19782179, compound

HRID 1612980Notes

Reaction equation

HRID 1612980 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]2[C:3]=1[CH2:4][CH:5]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:6]2=O>C(O)C.[Pd]>[OH:11][C:8]1[CH:9]=[CH:10][C:2]([F:1])=[C:3]2[C:7]=1[CH2:6][CH:5]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:4]2

Participants

4

Reactant 1

HCID 19782213Ethyl 4-fluoro-2,3-dihydro-7-hydroxy-1-oxo-1H-indene-2-carboxylate

Product 1

HCID 19782179HCID 19782179, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

94 g (0.4 mol) of the compound from Example 26 are hydrogenated in 600 ml of ethanol using 20 g of Pd-C (5% strength) at 30 bar of H2 and 60° C. for 4 h. The catalyst is filtered off, the solution is evaporated and the residue is flash chromatographed on silica gel (eluent: petroleum ether/acetone 5:1). After evaporating the fractions containing the product, the residue is recrystallized from ligroin.

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe solution is evaporated
  3. customchromatographed on silica gel (eluent: petroleum ether/acetone 5:1)
  4. customAfter evaporating the fractions
  5. additioncontaining the product
  6. customthe residue is recrystallized from ligroin

Sources & evidence

ORD record
ord-15b6ded214fa49d8b4642688f9d427ca
Source dataset
uspto-grants-1993_03
Patent number
US05191092

Reaction notes

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