Ethyl Acetate → 5-[(E)-2-phenylethenyl]-1,2,4-oxadiazole

HRID 967754

반응식

HRID 967754 반응식
O[NH:2][CH:3]=[N:4][C:5](=[O:14])[CH:6]=[CH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C([O-])([O-])=O.[K+].[K+].C(OCC)(=O)C>C(O)(=O)C.O1CCOCC1>[C:8]1(/[CH:7]=[CH:6]/[C:5]2[O:14][N:2]=[CH:3][N:4]=2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 178520452HCID 178520452, 화합물

생성물 1

HCID 222913425-[(E)-2-phenylethenyl]-1,2,4-oxadiazole수율 8%

시약·촉매·용매 1

HCID 22565020HOAc dioxane용매

실험 절차

N-[(Hydroxyamino)methylene]-cinnamamide (850 mg, 4.5 mmol) was dissolved in acetic acid/dioxane (20 mL 1:1 v:v), and heated to reflux for 2 h. The cooled solution was made basic (pH 8) with K2CO3, and partitioned between ethyl acetate and water. The organics were dried over Na2SO4, and concentrated in vacuo. The resultant solids were triturated with hot ethyl acetate, and the soluble portion was purified by flash column chromatography on silica eluting with 2:1 hexane:ethyl acetate to afford 5-[(E)-2-phenylethenyl]-1,2,4-oxadiazole (60 mg, 8% yield) as a white powder. M.p. 53–55° C. 1H NMR (CDCl3, 300 MHz) δ8.43 (s, 1H), 7.85 (d, J=16 Hz, 1H), 7.60 (m, 2H), 7.45 (m, 3H), 7.05 (d, J=16 Hz, 1H). MS (EI ionization) 171 (M+−H).

후처리

  1. temperatureheated
  2. temperatureto reflux for 2 h
  3. custompartitioned between ethyl acetate and water
  4. dry with materialThe organics were dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe resultant solids were triturated with hot ethyl acetate
  7. customthe soluble portion was purified by flash column chromatography on silica eluting with 2:1 hexane

출처 및 근거

ORD 기록
ord-6ad1428dd2c64d83a156f20351cef2f1
출처 데이터셋
uspto-grants-2005_10
특허 번호
US06956049B1

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