HCID 19822204, compound → HCID 19822257, compound

HRID 1030407Notes

Reaction equation

HRID 1030407 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[C:15]([CH3:22])([CH3:21])[CH2:16][C:17]([CH3:20])([CH3:19])[CH3:18])[O:11][C:10]([CH3:34])([CH2:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([N+:31]([O-])=O)=[CH:27][CH:26]=1)[CH2:9][C:8]2=[O:35])(=[O:3])[CH3:2].[H][H]>CO.C1C=CC=CC=1.[Pd]>[C:1]([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[C:15]([CH3:22])([CH3:21])[CH2:16][C:17]([CH3:20])([CH3:18])[CH3:19])[O:11][C:10]([CH2:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([NH2:31])=[CH:27][CH:26]=1)([CH3:34])[CH2:9][C:8]2=[O:35])(=[O:3])[CH3:2]

Participants

6

Reactant 2

HCID 19822204HCID 19822204, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19822257HCID 19822257, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 241BenzeneSolventHCID 887MethanolSolvent

Procedure

12.3 g of 6-acetoxy-2-methyl-2-(4-nitrophenoxymethyl)-7-(1,1,3,3-tetramethylbutyl)chroman-4-one (prepared as described in Preparation 19) were dissolved in a mixture of 200 ml of methanol and 20 ml of benzene, and then catalytically reduced for 6 hours at room temperature, in the presence of 2.4 g of 10% w/w palladium-on-carbon, under 1 atmosphere (about 1 bar) pressure of hydrogen. The catalyst was filtered off, and the filtrate was condensed by evaporation under reduced pressure. The residue was purified by silica gel column chromatography, eluted with a 4:1 by volume mixture of benzene and ethyl acetate, to give the title compound.

Workup

  1. filtrationThe catalyst was filtered off
  2. customcondensed
  3. customby evaporation under reduced pressure
  4. customThe residue was purified by silica gel column chromatography
  5. washeluted with a 4:1 by volume mixture of benzene and ethyl acetate

Sources & evidence

ORD record
ord-4de6734790cb47189ec204e031882353
Source dataset
uspto-grants-1992_04
Patent number
US05104888

Reaction notes

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