Acetone → Ethyl 6-[(prop-2-en-1-yl)oxy]-1H-indole-2-carboxylate

HRID 255507Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 255507
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[NH:8]2)=[CH:4][CH:3]=1.[CH2:16](Br)[CH:17]=[CH2:18].C([O-])([O-])=O.[K+].[K+].CC(C)=O>[Cl-].[Na+].O>[CH2:18]([O:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[NH:8]2)=[CH:4][CH:3]=1)[CH:17]=[CH2:16]

Komponenten

6

Edukt 4

HCID 180AcetoneHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 18459473HCID 18459473, Verbindung

Produkt 1

HCID 13203761Ethyl 6-[(prop-2-en-1-yl)oxy]-1H-indole-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

Ethyl 6-hydroxy-1H-indole-2-carboxylate (4.6 g, 0.02 M) was heated under reflux with allylbromide (3 g, 2.2 ml, 0.025 M), K2CO3 (4.14 g 0.03 M) and acetone (150 ml) for 20 hours. On cooling the mixture was poured into brine and extracted into ethyl acetate, washed with brine, dried over magnesium sulphate and evaporated to dryness. The resulting crude brown solid was purified by extraction into hot 60°-80° petroleum ether to yield a yellow solid which was dried in vacuo, 4 g, 72%, mp 89°-91°.

Aufarbeitung

  1. temperatureOn cooling the mixture
  2. extractionextracted into ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over magnesium sulphate
  5. customevaporated to dryness
  6. customThe resulting crude brown solid was purified by extraction into hot 60°-80° petroleum ether
  7. customto yield a yellow solid which
  8. customwas dried in vacuo, 4 g, 72%, mp 89°-91°

Quellen und Nachweise

ORD-Eintrag
ord-f734b12ab828442bb6c58dbc36ee71c8
Quelldatensatz
uspto-grants-1987_10
Patentnummer
US04698345

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