Acetic Acid → HCID 67486594, compound

HRID 729702Notes

Reaction equation

HRID 729702 reaction equation
CC[O-].[Na+].[CH2:5]([O:7][C:8](=[O:21])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH:20]=[CH:19][N:18]=[N:17]2)=[CH:12][CH:11]=1)[CH3:6].[O:22]1[CH2:27][CH2:26][CH:25]([CH:28]=O)[CH2:24][CH2:23]1.CC(O)=O>CCO.CS(C)=O.CCOC(C)=O>[O:22]1[CH2:27][CH2:26][CH:25]([CH:28]=[C:9]([C:10]2[CH:11]=[CH:12][C:13]([N:16]3[CH:20]=[CH:19][N:18]=[N:17]3)=[CH:14][CH:15]=2)[C:8]([O:7][CH2:5][CH3:6])=[O:21])[CH2:24][CH2:23]1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 2723922Sodium ethoxideHCID 9964078Tetrahydro-2H-pyran-4-carboxaldehydeHCID 14196994HCID 14196994, compound

Product 1

HCID 67486594HCID 67486594, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

NaOEt (0.63 mL of a 0.5M solution in EtOH, 0.32 mmol) was added dropwise to a stirred solution of ethyl(4-[1,2,3]triazol-1-ylphenyl)acetate (730 mg, 3.16 mmol) and tetrahydropyran-4-carboxaldehyde (396 mg, 3.47 mmol) in anhydrous DMSO (3 mL). The mixture was heated at 80° C. for 16 h, before being treated with AcOH to adjust the pH to 7. EtOAc (30 mL) was added, then the solution was washed with H2O (2×10 mL) and brine (10 mL), before being dried (MgSO4). Filtration, solvent evaporation, and column chromatography (IH-EtOAc, 1:1) yielded ethyl 3-(tetrahydropyran-4-yl)-2(4-[1,2,3]triazol-1-ylphenyl)acrylate: m/z (ES+)=328.2 [M+H]+. This ester (404 mg, 1.23 mmol) was saponified as described above in Preparation 25 to give the title compound: m/z (ES+)=300.2 [M+H]+.

Workup

  1. washthe solution was washed with H2O (2×10 mL) and brine (10 mL)
  2. dry with materialbefore being dried (MgSO4)
  3. filtrationFiltration, solvent evaporation, and column chromatography (IH-EtOAc, 1:1)

Sources & evidence

ORD record
ord-15543287d5f34119b010764eb0409746
Source dataset
uspto-grants-2009_09
Patent number
US07582632B2

Reaction notes

Loading…