Sodium hydride → Ethyl acetate hexane

HRID 581398

Reaktionsgleichung

Reaktionsgleichung von HRID 581398
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:18])[N:6]2[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[H-].[Na+].Br[CH:22]([CH3:27])[C:23]([O:25][CH3:26])=[O:24]>CN(C=O)C>[CH3:26][O:25][C:23](=[O:24])[CH:22]([O:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:18])[N:6]2[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:27].[CH3:22][CH2:23][O:24][C:2]([CH3:10])=[O:1].[CH3:9][CH2:10][CH2:2][CH2:3][CH2:4][CH3:5]

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 95576Methyl 2-bromopropionateHCID 107523601-Benzyl-2-methyl-1H-indol-4-ol

Produkt 2

HCID 106396522-[[2-methyl-1-(phenylmethyl)-1H-indol-4-yl]oxy]propanoic acid methyl esterHCID 21226206Ethyl acetate hexaneAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

4-Hydroxy-2-methyl-1-(phenylmethyl)-1H-indole (483 mg, 2.0 mmol) was reacted with 82 mg (2.0 mmol) of 60% NaH/mineral oil in 20 mL of DMF and then with 0.22 mL(2.0 mmol) of dl-methyl 2-bromopropionate as described in Example 1, Part E to give after chromatography on silica gel eluting with 20% EtOAc/hexane 480 mg (74% yield) of dl-2-[[2-methyl-1-(phenylmethyl)-1H-indol-4-yl]oxy]propanoic acid methyl ester.

Quellen und Nachweise

ORD-Eintrag
ord-0e987fd4abed43fea0d0507d1fe691e3
Quelldatensatz
uspto-grants-1999_07
Patentnummer
US05919943

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