Ethanol → methyl-(2E)-3-methyl-5-[(1-phenyl-1-H-tetrazol-5-yl)thio]pent-2-enoate

HRID 1160584Notes

Reaction equation

HRID 1160584 reaction equation
OO.C(O)C.[CH2:6]([O:8][C:9](=[O:27])/[CH:10]=[C:11](\[CH3:26])/[CH2:12][CH2:13][S:14][C:15]1[N:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:18]=[N:17][N:16]=1)C>C(OCC)(=O)C>[CH3:6][O:8][C:9](=[O:27])/[CH:10]=[C:11](\[CH3:26])/[CH2:12][CH2:13][S:14][C:15]1[N:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:18]=[N:17][N:16]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 784Hydrogen PeroxideHCID 59516418ethyl-(2E)-3-methyl-5-[(1-phenyl-1-H-tetrazol-5-yl)thio]pent-2-enoate

Product 1

HCID 59516421methyl-(2E)-3-methyl-5-[(1-phenyl-1-H-tetrazol-5-yl)thio]pent-2-enoateYield 99.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

About 30% hydrogen peroxide solution (47.4 ml, 418.0 mmol) solution of hexaammonium heptamolybdate tetrahydrate (542 mg, 0.44 mmol) was added to an ethanol (200 ml) solution of ethyl-(2E)-3-methyl-5-[(1-phenyl-1-H-tetrazol-5-yl)thio]pent-2-enoate (13.31 g, 41.80 mmol) at room temperature. After stirred for at the same temperature for 12 hours, the reaction solution was diluted with ethyl acetate and washed with distilled water and brine. After the organic layer was dried over anhydrous sodium sulfate and the drying agent was filtered off, the organic layer was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (Merck, commercial name Silica Gel 60, 230-400 mesh; hexane:ethyl acetate=4:1) to obtain the title compound (12.65 g) as a white solid.

Workup

  1. washwashed with distilled water and brine
  2. dry with materialAfter the organic layer was dried over anhydrous sodium sulfate
  3. filtrationthe drying agent was filtered off
  4. concentrationthe organic layer was concentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (Merck, commercial name Silica Gel 60, 230-400 mesh; hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-954b3139024747e8adb832e3ddc5be8f
Source dataset
uspto-grants-2010_10
Patent number
US07816401B2

Reaction notes

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