Acetic Acid → HCID 67486594, compound

HRID 1350295Notes

Reaction equation

HRID 1350295 reaction equation
CC[O-].[Na+].[N:5]1([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:12][CH:11]=2)[CH:9]=[CH:8][N:7]=[N:6]1.[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:16]([C:13]2[CH:12]=[CH:11][C:10]([N:5]3[CH:9]=[CH:8][N:7]=[N:6]3)=[CH:15][CH:14]=2)[C:17]([O:19][CH2:20][CH3:21])=[O:18])[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-48844249c6fc4d94a882458b4adf031e
Source dataset
uspto-grants-2007_05
Patent number
US07214681B2

Reaction notes

Loading…