Pyridine → Methyl 3-(5-phenyl-1,3,4-oxadiazol-2-yl)propanoate

HRID 1664563Notes

Reaction equation

HRID 1664563 reaction equation
S(Cl)(Cl)=O.[C:5]([NH:13][NH:14][C:15](=[O:22])[CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])(=O)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.N1C=CC=CC=1>O1CCCC1>[C:6]1([C:5]2[O:22][C:15]([CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])=[N:14][N:13]=2)[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 569517Methyl 4-(2-benzoylhydrazino)-4-oxobutanoate

Product 1

HCID 57600262Methyl 3-(5-phenyl-1,3,4-oxadiazol-2-yl)propanoateYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Thionyl chloride (0.34 mL, 4.7 mmol) was added to the mixture of methyl 4-(2-benzoylhydrazino)-4-oxobutanoate (900 mg, 4 mmol), Pyridine (0.87 mL, 0.011 mol) in tetrahydrofuran (20 mL) at room temperature. After stirring for 3 hours, the reaction mixture was concentrated. The residue was mixed with toluene (20 mL) and refluxed overnight. The reaction was diluted with water and extracted with ethyl acetate three times. The combined organic layers were dried with sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography to yield the desired product (600 mg, 72%). LCMS calculated for C12H13N2O3 (M+H): 233.1. found: 233.1.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. additionThe residue was mixed with toluene (20 mL)
  3. temperaturerefluxed overnight
  4. additionThe reaction was diluted with water
  5. extractionextracted with ethyl acetate three times
  6. dry with materialThe combined organic layers were dried with sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-ac28907c015040ce88a80ec4d3cbafc9
Source dataset
uspto-grants-2011_10
Patent number
US08039478B2

Reaction notes

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