HCID 131721447, compound → HCID 70237824, compound

HRID 1602746Notes

Reaction equation

HRID 1602746 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([O:18][CH3:19])=[CH:15][CH:16]=3)[O:11][CH2:10][C:9]=2[C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=2)=[CH:4][CH:3]=1>[Pd].C(O)C>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C:17]3[C:12](=[CH:13][C:14]([O:18][CH3:19])=[CH:15][CH:16]=3)[O:11][CH2:10][C@H:9]2[C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:27])[F:28])=[CH:22][CH:21]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 131721447HCID 131721447, compound

Product 1

HCID 70237824HCID 70237824, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Palladium on carbon (10%, 0.40 g, 0.4 mmol) was added to a stirred solution of 4-(4-hydroxyphenyl)-7-methoxy-3-(4-(trifluoromethyl)phenyl)chrom-3-ene (2.99 g, 7.51 mmol) in ethanol, (100 ml) and the mixture hydrogenated at room temperature for 24 h. The catalyst was removed by filtration, and the solvent evaporated to give an off-white solid which was purified by recrystallisation from 50 ml ethanol. This gave the first crop of product as colourless needles. The mother liquors were evaporated and the recrystallisation repeated from aqueous ethanol, to give a second crop of colourless needles. The solids were combined and vacuum dried.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent evaporated
  3. customto give an off-white solid which
  4. customwas purified by recrystallisation from 50 ml ethanol
  5. customThis gave the first crop of product as colourless needles
  6. customThe mother liquors were evaporated
  7. customthe recrystallisation
  8. customto give a second crop of colourless needles
  9. customvacuum dried

Sources & evidence

ORD record
ord-7f6ef155e89940d3a798ca53a2c3f62e
Source dataset
uspto-grants-1999_11
Patent number
US05985306

Reaction notes

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