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

HRID 1664563ノート

反応式

HRID 1664563 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ac28907c015040ce88a80ec4d3cbafc9
出典データセット
uspto-grants-2011_10
特許番号
US08039478B2

反応ノート

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