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

HRID 258025Notes

Reaction equation

HRID 258025 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-1420c2fe9cad409e8f0864028f83b91f
Source dataset
uspto-grants-1993_11
Patent number
US05264458

Reaction notes

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