Ethyl 3-(3-ethoxy-3-oxopropyl)-1H-indole-2-carboxylate → ethyl 3-(3-hydroxypropyl)-1H-indole-2-carboxylate

HRID 1013272Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1013272
C([O:3][C:4](=O)[CH2:5][CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][C:8]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17])C.B.C1COCC1>C1COCC1>[OH:3][CH2:4][CH2:5][CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][C:8]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17]

Komponenten

4

Edukt 2

HCID 612032Ethyl 3-(3-ethoxy-3-oxopropyl)-1H-indole-2-carboxylateHCID 2723981Borane;tetrahydrofuran

Produkt 1

HCID 67316234ethyl 3-(3-hydroxypropyl)-1H-indole-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a mixture of ethyl 3-(3-ethoxy-3-oxopropyl)-1H-indole-2-carboxylate (2.82 g) in THF (40 mL) was added IM borane-THF (40 mL). The mixture was stirred at room temperature for 16 hours, quenched with methanol (100 mL) and concentrated. The concentrate was purified by flash column chromatography on silica gel with 5-25% ethyl acetate/hexanes.

Aufarbeitung

  1. customquenched with methanol (100 mL)
  2. concentrationconcentrated
  3. customThe concentrate was purified by flash column chromatography on silica gel with 5-25% ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-10a0382ed8b54d5796c9f3d1eccf01e0
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07981888B2

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