Methyl iodide → tert-butyl 2-(1-ethoxy-1-oxopropan-2-yl)-1H-indole-1-carboxylate

HRID 1847499Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1847499
[CH2:1]([O:3][C:4](=[O:22])[CH2:5][C:6]1[N:7]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH3:2].[CH3:23][Si](C)(C)N[Si](C)(C)C.[K].CI>C1COCC1>[CH2:1]([O:3][C:4](=[O:22])[CH:5]([C:6]1[N:7]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH3:23])[CH3:2]

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 45051783Silanamine, 1,1,1-trimethyl-N-(trimethylsilyl)-, potassium saltHCID 53419936tert-Butyl 2-(2-ethoxy-2-oxoethyl)-1H-indole-1-carboxylate

Produkt 1

HCID 59129246tert-butyl 2-(1-ethoxy-1-oxopropan-2-yl)-1H-indole-1-carboxylateAusbeute 89,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

tert-Butyl 2-(2-ethoxy-2-oxoethyl)-1H-indole-1-carboxylate (3.0 g, 9.9 mmol) was added to anhydrous THF (29 mL) and cooled to −78° C. A 0.5M solution of potassium hexamethyldisilazane (20 mL, 9.9 mmol) was added slowly such that the internal temperature stayed below −60° C. Stirring was continued for 1 h at −78° C. Methyl iodide (727 μL, 11.7 mmol) was added to the mixture. The mixture was stirred for 30 minutes at room temperature. The mixture was quenched with sat. aq. ammonium chloride and partitioned between water and dichloromethane. The aqueous phase was extracted with dichloromethane and the combined organic phases were dried over Na2SO4 and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (ethylacetate/hexane=1/9) to give tert-butyl 2-(1-ethoxy-1-oxopropan-2-yl)-1H-indole-1-carboxylate (2.8 g, 88%).

Aufarbeitung

  1. customstayed below −60° C
  2. stirringThe mixture was stirred for 30 minutes at room temperature
  3. customThe mixture was quenched with sat. aq. ammonium chloride
  4. custompartitioned between water and dichloromethane
  5. extractionThe aqueous phase was extracted with dichloromethane
  6. dry with materialthe combined organic phases were dried over Na2SO4
  7. customevaporated under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel (ethylacetate/hexane=1/9)

Quellen und Nachweise

ORD-Eintrag
ord-be4064a3578b4fe2bfc0ebf6b4c26e7c
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08952050B2

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