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Acetyl chloride → 1-[2-(3-Ethyl-5-methyl-1,2-oxazol-4-yl)-1H-indol-3-yl]ethan-1-one

HRID 358404
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 358404
[CH2:1]([C:3]1[C:7]([C:8]2[NH:9][C:10]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][CH:11]=3)=[C:6]([CH3:17])[O:5][N:4]=1)[CH3:2].[C:18](Cl)(=[O:20])[CH3:19]>FC(F)(F)S([O-])(=O)=O.[Ag+].C(Cl)Cl>[CH2:1]([C:3]1[C:7]([C:8]2[NH:9][C:10]3[C:15]([C:16]=2[C:18](=[O:20])[CH3:19])=[CH:14][CH:13]=[CH:12][CH:11]=3)=[C:6]([CH3:17])[O:5][N:4]=1)[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 6367Acetyl chlorideHCID 130386862-(3-Ethyl-5-methyl-1,2-oxazol-4-yl)-1H-indole

Produkt 1

HCID 128514531-[2-(3-Ethyl-5-methyl-1,2-oxazol-4-yl)-1H-indol-3-yl]ethan-1-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 76223Silver(I) trifluoromethanesulfonateKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of 33.5 g. (0.148 mole) of 2-(3-ethyl-5-methyl-4-isoxazolyl)-indole in 450 ml. methylene chloride is treated by the portionwise addition of 41.8 g. (0.163 mole) of silver trifluoromethanesulfonate. The resulting suspension is then treated by the dropwise addition of 12.8 g. (0.163 mole) of acetyl chloride in 50 ml. methylene chloride. The temperature rises to 35° C. during the addition. After the addition is complete the mixture is stirred at room temperature for 4 hours and then filtered. The filtrate is washed with 150 ml. 2N sodium hydroxide, water and 2N sodium hydroxide dried over anhydrous magnesium sulfate and evaporated in vacuo to given an oil. The oil is crystallized from ether to give 2-(3-ethyl-5-methyl-4-isoxazolyl)-3-acetyl indole, m.p. 170°-173° C.

Aufarbeitung

  1. additionThe resulting suspension is then treated by the dropwise addition of 12.8 g
  2. additionThe temperature rises to 35° C. during the addition
  3. additionAfter the addition
  4. filtrationfiltered
  5. washThe filtrate is washed with 150 ml
  6. dry with material2N sodium hydroxide, water and 2N sodium hydroxide dried over anhydrous magnesium sulfate
  7. customevaporated in vacuo
  8. customThe oil is crystallized from ether

Quellen und Nachweise

ORD-Eintrag
ord-bcdf2fbf26a547f4bfe93c44485e73ca
Quelldatensatz
uspto-grants-1984_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04467096

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