HCID 13605827, compound → HCID 20245713, compound

HRID 1589708Notes

Reaction equation

HRID 1589708 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)[CH2:9][C:8]2=[O:31])(=[O:3])[CH3:2].[H][H]>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:26]=[CH:25][C:24]([NH2:27])=[CH:23][CH:22]=1)([CH3:30])[CH2:9][C:8]2=[O:31])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 13605827HCID 13605827, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20245713HCID 20245713, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

In a similar manner to Preparation 44, 0.9 g of 6-acetoxy-7-t-butyl-2-methyl-2-(4-nitrophenoxymethyl)chroman-4-one was dissolved in 20 ml of acetic acid, and catalytic hydrogenation was performed for 5.5 hours with a hydrogen pressure of 45-55 lb/sq. inch (3.1-3.8 bars), using Pearl's apparatus, in the presence of 0.4 g of 10% w/w palladium-on-carbon. The palladium-on-carbon was removed by filtration from the reaction mixture and washed with acetic acid. The filtrate and the washings were combined, and the mixture was poured into ice-water, neutralized with sodium carbonate, and extracted with benzene. The benzene extract was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was subjected to silica gel column chromatography, eluted with a 5:1 by volume mixture of benzene and ethyl acetate, to give the desired 6-acetoxy-2-(4-aminophenoxymethyl)-7-t-butyl-2-methylchroman-4-one.

Workup

  1. customThe palladium-on-carbon was removed by filtration from the reaction mixture
  2. washwashed with acetic acid
  3. additionthe mixture was poured into ice-water
  4. extractionextracted with benzene
  5. extractionThe benzene extract
  6. washwas washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThe solvent was distilled off
  9. washeluted with a 5:1 by volume mixture of benzene and ethyl acetate

Sources & evidence

ORD record
ord-e19f5e74206f47bf83fb0b458e667bd9
Source dataset
uspto-grants-1986_02
Patent number
US04572912

Reaction notes

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