HCID 53676307, compound → HCID 57011853, compound

HRID 635827Notes

Reaction equation

HRID 635827 reaction equation
[F:1][CH:2]([F:21])[O:3][C:4]1[CH:9]=[C:8]([C@@H:10]2[CH2:15][CH:14]=[CH:13][CH2:12][C@@H:11]2[N+:16]([O-])=O)[CH:7]=[CH:6][C:5]=1[O:19][CH3:20].[H][H]>C(O)C.[Ni]>[F:1][CH:2]([F:21])[O:3][C:4]1[CH:9]=[C:8]([C@@H:10]2[CH2:15][CH2:14][CH2:13][CH2:12][C@@H:11]2[NH2:16])[CH:7]=[CH:6][C:5]=1[O:19][CH3:20]

Participants

5

Reactant 2

HCID 53676307HCID 53676307, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57011853HCID 57011853, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

14.6 g of (+/−)-cis-2-difluoromethoxy-1-methoxy-4-(2-nitrocyclohex-4-enyl)benzene are dissovled in 170 ml of ethanol, admixed with 3.0 g of Raney nickel and hydrogenated in an autoclave at a hydrogen pressure of 50 bar for 9 days. The suspension is filtered, the solvent is removed under reduced pressure and the residue is chromatographed over silica gel using a mixture of toluene/dioxane/triethylamine 3/1/0.5. Concentration of the appropriate fractions gives 3.4 g (25.7% of Th.) of the title compound as an oil.

Workup

  1. filtrationThe suspension is filtered
  2. customthe solvent is removed under reduced pressure
  3. customthe residue is chromatographed over silica gel using
  4. additiona mixture of toluene/dioxane/triethylamine 3/1/0.5

Sources & evidence

ORD record
ord-ae24f38044ec4e4587dc9df7d71c390e
Source dataset
uspto-grants-2001_02
Patent number
US06191138B1

Reaction notes

Loading…