p-Toluenesulfonic acid → 3-[5-(Phenylmethyl)-1,2,4-oxadiazol-3-yl]propanal

HRID 1097677Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1097677
C([O:3][CH:4](OCC)[CH2:5][CH2:6][C:7]1[N:11]=[C:10]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[O:9][N:8]=1)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>CCO>[C:13]1([CH2:12][C:10]2[O:9][N:8]=[C:7]([CH2:6][CH2:5][CH:4]=[O:3])[N:11]=2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Komponenten

4

Edukt 2

HCID 6101p-Toluenesulfonic acidHCID 668129523-[3,3-Bis(ethyloxy)propyl]-5-(phenylmethyl)-1,2,4-oxadiazole

Produkt 1

HCID 866431133-[5-(Phenylmethyl)-1,2,4-oxadiazol-3-yl]propanalAusbeute 89,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Crude 3-[3,3-bis(ethyloxy)propyl]-5-(phenylmethyl)-1,2,4-oxadiazole (5.63 g, 19.4 mmol) in EtOH (75 ml) was stirred with p-toluenesulphonic acid (0.738 g, 3.9 mmol) for 21 h and the mixture partitioned between EtOAc and water. The organics were isolated washed with water and brine, dried and concentrated to a red oil. This material contained significant amounts of acetal, therefore the oil was dissolved in THF (15 ml) and treated with 2M HCl solution for 2 h then partitioned between EtOAc and water. The organics were isolated washed with brine, dried and concentrated to yield 3-[5-(phenylmethyl)-1,2,4-oxadiazol-3-yl]propanal as a red/brown oil (3.77 g) which was used crude in the next stage.

Aufarbeitung

  1. customthe mixture partitioned between EtOAc and water
  2. customThe organics were isolated
  3. washwashed with water and brine
  4. customdried
  5. concentrationconcentrated to a red oil
  6. dissolutionthe oil was dissolved in THF (15 ml)
  7. additiontreated with 2M HCl solution for 2 h
  8. customthen partitioned between EtOAc and water
  9. customThe organics were isolated
  10. washwashed with brine
  11. customdried
  12. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-0cd3cb331f5641daa9cc2fb8ba8eadb5
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08143264B2

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