tert-butyl 2-(1-ethoxy-1-oxopropan-2-yl)-1H-indole-1-carboxylate → Ethyl 2-(1H-indol-2-yl)propanoate

HRID 468430Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 468430
[CH2:1]([O:3][C:4](=[O:23])[CH:5]([C:7]1[N:8](C(OC(C)(C)C)=O)[C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH3:6])[CH3:2]>ClCCl.C(O)(C(F)(F)F)=O>[NH:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:15]=[C:7]1[CH:5]([CH3:6])[C:4]([O:3][CH2:1][CH3:2])=[O:23]

Komponenten

4

Edukt 1

HCID 59129246tert-butyl 2-(1-ethoxy-1-oxopropan-2-yl)-1H-indole-1-carboxylate

Produkt 1

HCID 10921945Ethyl 2-(1H-indol-2-yl)propanoateAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

tert-Butyl 2-(1-ethoxy-1-oxopropan-2-yl)-1H-indole-1-carboxylate (2.77 g, 8.74 mmol) was dissolved in dichloromethane (25 mL) before TFA (9.8 mL) was added. The mixture was stirred for 1.5 h at room temperature. The mixture was evaporated to dryness, taken up in dichloromethane and washed with sat. aq. sodium bicarbonate, water, and brine. The product was purified by column chromatography on silica gel (0-20% EtOAc in hexane) to give ethyl 2-(1H-indol-2-yl)propanoate (0.92 g, 50%).

Aufarbeitung

  1. additionwas added
  2. customThe mixture was evaporated to dryness
  3. washwashed with sat. aq. sodium bicarbonate, water, and brine
  4. customThe product was purified by column chromatography on silica gel (0-20% EtOAc in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-50aeb0e3cc664db6a78afc13c517dfc7
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08623905B2

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