Sodium hydride → (1-Benzyl-2-ethyl-1H-indol-4-yloxy)-acetic acid methyl ester

Reaktionsgleichung

[CH2:1]([C:3]1[N:4]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:5]2[C:10]([CH:11]=1)=[C:9]([OH:12])[CH:8]=[CH:7][CH:6]=2)[CH3:2].[H-].[Na+].Br[CH2:23][C:24]([O:26][CH3:27])=[O:25]>>[CH3:27][O:26][C:24](=[O:25])[CH2:23][O:12][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[CH:11]=[C:3]([CH2:1][CH3:2])[N:4]2[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Komponenten

Edukt 3

HCID 24758Sodium hydride

HCID 60984Methyl bromoacetate

HCID 98164161-Benzyl-2-ethyl-1H-indol-4-OL

Produkt 1

HCID 10687371(1-Benzyl-2-ethyl-1H-indol-4-yloxy)-acetic acid methyl esterAusbeute 69 %

Versuchsvorschrift

Using the procedure described in Example 1, Part E, 2-ethyl-4-hydroxy-1-(phenylmethyl)-1H-indole (1.56 g, 6.2 mmol) was treated with 248 mg (6.2 mmol) of 60% NaH/mineral oil and then 0.6 mL (6.2 mmol) of methyl bromoacetate. The product was purified by chromatography over silica gel eluting with 20% EtOAc/hexane, to give 1.37 g (69% yield) of [[2-ethyl-1-(phenylmethyl)-1H-indol-4-yl]oxy]acetic acid methyl ester, 89°-92° C.

Aufarbeitung

customThe product was purified by chromatography over silica gel eluting with 20% EtOAc/hexane

Quellen und Nachweise

ORD-Eintrag: ord-093410cd99d04309ae041c581fea5247
Quelldatensatz: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05733923

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