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Water → Methyl 1-(2,4,6-triisopropylphenylsulfonyl)-indole-3-propionate

HRID 129225
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 129225
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:12][CH2:13][C:14]([O:16][CH2:17]C)=[O:15])=[CH:4]1.[CH:19]([C:22]1[CH:27]=[C:26]([CH:28]([CH3:30])[CH3:29])[CH:25]=[C:24]([CH:31]([CH3:33])[CH3:32])[C:23]=1[S:34](Cl)(=[O:36])=[O:35])([CH3:21])[CH3:20].O>CCCCCC.CN(C=O)C>[CH:19]([C:22]1[CH:27]=[C:26]([CH:28]([CH3:29])[CH3:30])[CH:25]=[C:24]([CH:31]([CH3:33])[CH3:32])[C:23]=1[S:34]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:4]1)(=[O:36])=[O:35])([CH3:20])[CH3:21]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 810422,4,6-Tris(1-methylethyl)benzenesulfonyl chlorideHCID 225390Ethyl 3-(1h-indol-3-yl)propanoate

Produkt 1

HCID 54454025Methyl 1-(2,4,6-triisopropylphenylsulfonyl)-indole-3-propionateAusbeute 102,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228
Dimethylformamide
Lösungsmittel
2×
HCID 8058HexaneLösungsmittel

Versuchsvorschrift

Sodium hydride (60% oil 19.03 g 0.476 mol) was washed with n-hexane, and was suspended in DMF (500 ml). To the suspension was gradually added a solution of ethyl indole-3-propionate acid (64.79 g 0.317 mol) in DMF(100 ml). The mixture was stirred for one hour at 40°-50° C., and to the mixture was gradually added, under ice-cooling, 2,4,6-triisopropylphenylsulfonyl chloride (115.25 g, 0.38 mol), followed by stirring for one hour at room temperature. To the reaction mixture was added water (150 ml), and the mixture was subjected to extraction with n-hexane (500 ml). The extract solution was washed with water (100 ml) and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to to leave the title compound (152 g).

Aufarbeitung

  1. additionto the mixture was gradually added, under ice-
  2. temperaturecooling
  3. stirringby stirring for one hour at room temperature
  4. extractionthe mixture was subjected to extraction with n-hexane (500 ml)
  5. washThe extract solution was washed with water (100 ml)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-78e1ca464ff94ab8b8643cb95e67bbf5
Quelldatensatz
uspto-grants-1995_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05466689

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