HCID 14515031, compound → HCID 14515032, compound

HRID 264713Notes

Reaction equation

HRID 264713 reaction equation
C([O:8][C:9]1[C:14]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)=[CH:13][C:12]([CH:22]([CH3:24])[CH3:23])=[CH:11][C:10]=1[CH:25]([CH3:27])[CH3:26])C1C=CC=CC=1.[H][H]>C(OCC)(=O)C.C(O)(=O)C.[Pd]>[CH:25]([C:10]1[CH:11]=[C:12]([CH:22]([CH3:24])[CH3:23])[CH:13]=[C:14]([C:15]2[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=2)[C:9]=1[OH:8])([CH3:26])[CH3:27]

Participants

6

Reactant 2

HCID 14515031HCID 14515031, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14515032HCID 14515032, compoundYield 92.9%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

4 g of 10% Pd on carbon are added to a solution of 49.3 g (0.136 mol) of the benzyl ether from step 4 in 1 l of ethyl acetate and 100 ml of glacial acetic acid and the mixture is shaken in a hydrogen atmosphere (vigorous absorption of H2) for 20 minutes. The catalyst is filtered off, the filtrate is concentrated, the residue is taken up several times in toluene and the solution is in each case concentrated in vacuo. 34.4 g of the title compound are obtained as a colorless oil, b.p. 115° C./0.1 torr.

Workup

  1. filtrationThe catalyst is filtered off
  2. concentrationthe filtrate is concentrated
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-577e513e709b4d60883b746e5aae7478
Source dataset
uspto-grants-1997_07
Patent number
US05646272

Reaction notes

Loading…