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

HRID 503427Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 503427
[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-578604fc71da40b9b8b4b401f0825b3c
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07776905B2

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