5-{(E)-2-[4-(benzyloxy)-3-methylphenyl]ethenyl}-4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole → 2-Methyl-4-(2-{4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}ethyl)phenol

HRID 460019Notes

Reaction equation

HRID 460019 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[C:17]2[S:21][C:20]([C:22]3[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=3)=[N:19][C:18]=2[CH3:32])=[CH:11][C:10]=1[CH3:33])C1C=CC=CC=1>C(O)(=O)C.[Pd]>[CH3:33][C:10]1[CH:11]=[C:12]([CH2:15][CH2:16][C:17]2[S:21][C:20]([C:22]3[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=3)=[N:19][C:18]=2[CH3:32])[CH:13]=[CH:14][C:9]=1[OH:8]

Participants

4

Reactant 1

HCID 179721765-{(E)-2-[4-(benzyloxy)-3-methylphenyl]ethenyl}-4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole

Product 1

HCID 179535512-Methyl-4-(2-{4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}ethyl)phenol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 5-{(E)-2-[4-(benzyloxy)-3-methylphenyl]ethenyl}-4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole)_(intermediate 6, 1.5 g) in glacial acetic acid (30 ml) was hydrogenated over 10% palladium on carbon (0.150 g). The catalyst was filtered off, the solvent was removed and the residues dissolved in ethyl acetate. This was washed with saturated sodium bicarbonate solution and brine. Drying and removal of solvent gave an oil which was purified by SPE (Si cartridge). Elution with cyclohexane:ethyl acetate gave the title compound as a white solid.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent was removed
  3. dissolutionthe residues dissolved in ethyl acetate
  4. washThis was washed with saturated sodium bicarbonate solution and brine
  5. customDrying
  6. customremoval of solvent
  7. customgave an oil which
  8. customwas purified by SPE (Si cartridge)
  9. washElution with cyclohexane

Sources & evidence

ORD record
ord-d77754af1fba404c95d6c9f2053c34c4
Source dataset
uspto-grants-2007_03
Patent number
US07196107B2

Reaction notes

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