Sodium hydride → 5-{(E)-2-[4-(benzyloxy)-3-methylphenyl]ethenyl}-4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole

HRID 460018Notes

Reaction equation

HRID 460018 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=2)[S:5][C:6]=1[CH2:7]P(=O)(OCC)OCC.[H-].[Na+].[CH2:28]([O:35][C:36]1[CH:43]=[CH:42][C:39]([CH:40]=O)=[CH:38][C:37]=1[CH3:44])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>O1CCCC1>[CH2:28]([O:35][C:36]1[CH:43]=[CH:42][C:39](/[CH:40]=[CH:7]/[C:6]2[S:5][C:4]([C:16]3[CH:17]=[CH:18][C:19]([C:22]([F:23])([F:24])[F:25])=[CH:20][CH:21]=3)=[N:3][C:2]=2[CH3:1])=[CH:38][C:37]=1[CH3:44])[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 202986464-(Benzyloxy)-3-methylbenzaldehydeHCID 86592483Diethyl{4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}methylphosphonate2×

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of diethyl {4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}methylphosphonate (intermediate 4, 1.4 g) in dry tetrahydrofuran (10 ml) cooled in ice under nitrogen was added sodium hydride (0.12 g, 60% dispersion in mineral oil) and the reaction was stirred for 30 minutes. A solution of 4-benzyloxy-3-methylbenzaldehyde (0.724 g) in dry tetrahydrofuran (10 ml) was added drop-wise, the reaction was allowed to come to room temperature and stirred for 2 hours. The solvent was removed and the residues partitioned between water (50 ml) and chloroform (50 ml). The aqueous phase was extracted with chloroform (20 ml) and the combined organics were washed with water and dried. Removal of solvent gave a solid which was purified by SPE chromatography. Elution with cyclohexane:ethyl acetate (20:1) gave the title compound as a yellow solid.

Workup

  1. customto come to room temperature
  2. stirringstirred for 2 hours
  3. customThe solvent was removed
  4. customthe residues partitioned between water (50 ml) and chloroform (50 ml)
  5. extractionThe aqueous phase was extracted with chloroform (20 ml)
  6. washthe combined organics were washed with water
  7. customdried
  8. customRemoval of solvent
  9. customgave a solid which
  10. customwas purified by SPE chromatography
  11. washElution with cyclohexane:ethyl acetate (20:1)

Sources & evidence

ORD record
ord-31c14693321f4b3fbea2f24bd2b54cda
Source dataset
uspto-grants-2007_03
Patent number
US07196107B2

Reaction notes

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