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

HRID 323702

Reaktionsgleichung

Reaktionsgleichung von HRID 323702
[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

4

Edukt 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 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, in EP Publication No. 0 675 110, 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]oxyl]acetic acid methyl ester; mp 89-92° C.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-9b76f4e8300747e7a5f0afc07b641bf8
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06214855B1

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