Sodium hydride → 3-[3-(2-Phenyl-thiazol-4-ylmethoxy)-phenyl]-acrylic acid methyl ester

HRID 1444332Notes

Reaction equation

HRID 1444332 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([OH:12])[CH:7]=1.[H-].[Na+].Cl[CH2:17][C:18]1[N:19]=[C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[S:21][CH:22]=1>CN(C=O)C.CCCCCCC>[CH3:1][O:2][C:3](=[O:13])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH2:17][C:18]2[N:19]=[C:20]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[S:21][CH:22]=2)[CH:7]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 94283Methyl 3-(3-hydroxyphenyl)prop-2-enoateHCID 2369694-(Chloromethyl)-2-phenyl-1,3-thiazole

Product 1

HCID 684973673-[3-(2-Phenyl-thiazol-4-ylmethoxy)-phenyl]-acrylic acid methyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8900HeptaneSolvent

Procedure

3-(3-Hydroxy-phenyl)-acrylic acid methyl ester (85 mg, 0.48 mmol) was dissolved in dry DMF (1.5 ml) and NaH (14 mg, 0.60 mmol) was added as a suspension in heptane (0.5 ml). The mixture was stirred at room temperature for 10 min. 4-Chloromethyl-2-phenyl-thiazole (100 mg, 0.48 mmol) was added portion-wise and the solution left stirring for 4 h. The reaction mixture was quenched with H2O (2 ml) and extracted with EtOAc (3×1 ml). The combined organic layers were washed with H2O (3×1 ml), dried (MgSO4), filtered and the solvent removed in vacuo to give a mixture of acid and ester, which was used without further purification.

Workup

  1. waitthe solution left
  2. stirringstirring for 4 h
  3. customThe reaction mixture was quenched with H2O (2 ml)
  4. extractionextracted with EtOAc (3×1 ml)
  5. washThe combined organic layers were washed with H2O (3×1 ml)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent removed in vacuo
  9. customto give
  10. customwas used without further purification

Sources & evidence

ORD record
ord-ce880b5e635e4e1e9ed8c99afa42cf89
Source dataset
uspto-grants-2010_02
Patent number
US07662839B2

Reaction notes

Loading…