HCID 19822235, compound → HCID 19822255, compound

HRID 1030406Notes

Reaction equation

HRID 1030406 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)[CH:9]=[CH:8]2)(=[O:3])[CH3:2].[H][H]>[Pd].CO>[C:1]([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[C:15]([CH3:21])([CH3:22])[CH2:16][C:17]([CH3:20])([CH3:18])[CH3:19])[O:11][C:10]([CH2:23][O:24][C:25]1[CH:26]=[CH:27][C:28]([NH2:31])=[CH:29][CH:30]=1)([CH3:34])[CH2:9][CH2:8]2)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 19822235HCID 19822235, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19822255HCID 19822255, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Using Paar's hydrogenation apparatus, a mixture of 9.1 g of 6-acetoxy-2-methyl-2-(4-nitrophenoxymethyl)-7-(1,1,3,3-tetramethylbutyl)-2H-chromene (prepared as described in Preparation 21), 2g of 10% w/w palladium-on-carbon and 150 ml of methanol was stirred for 10 hours under 3-5 atmospheres (about 3-5-bars) 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 10:1 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 10:1 by volume mixture of benzene and ethyl acetate

Sources & evidence

ORD record
ord-5c4bbe751ee440b99549a9f2dae34277
Source dataset
uspto-grants-1992_04
Patent number
US05104888

Reaction notes

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