HCID 19822239, compound → HCID 19822172, compound

HRID 1030427Notes

Reaction equation

HRID 1030427 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[C:15]([CH3:18])([CH3:17])[CH3:16])[O:11][C:10]([CH3:30])([CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[CH:23][CH:22]=1)[CH:9]=[CH:8]2)(=[O:3])[CH3:2].[H][H]>C1C=CC=CC=1.C(O)(=O)C.[Pd]>[C:1]([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[C:15]([CH3:18])([CH3:16])[CH3:17])[O:11][C:10]([CH2:19][O:20][C:21]1[CH:22]=[CH:23][C:24]([NH2:27])=[CH:25][CH:26]=1)([CH3:30])[CH2:9][CH2:8]2)(=[O:3])[CH3:2]

Participants

6

Reactant 2

HCID 19822239HCID 19822239, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19822172HCID 19822172, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 241BenzeneSolvent

Procedure

2.1 g of 6-acetoxy-7-t-butyl-2-methyl-2-(4-nitrophenoxymethyl)-2H-chromene (prepared as described in Preparation 57) were dissolved in a mixture of 20 ml of benzene and 2 ml of acetic acid, and the compound was reduced for 10 hours at room temperature, in the presence of 0.1 g of 10% w/w palladium-on-carbon, and under about 1 atmosphere (about 1 bar) pressure of hydrogen. The catalyst was filtered off, and the reaction mixture was washed with a saturated aqueous solution of sodium bicarbonate and then with water, after which it was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography, eluted with benzene, to give the title compound as a slightly brown oil.

Workup

  1. filtrationThe catalyst was filtered off
  2. washthe reaction mixture was washed with a saturated aqueous solution of sodium bicarbonate
  3. dry with materialwith water, after which it was dried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe resulting residue was purified by silica gel column chromatography
  6. washeluted with benzene

Sources & evidence

ORD record
ord-76efeefdfdd54ddeb8f6336cf7c1d296
Source dataset
uspto-grants-1992_04
Patent number
US05104888

Reaction notes

Loading…