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Sodium hydride → 4-[2-(4-Tert-butylphenyl)ethoxy]-5-methoxy-6-methoxymethylpyrimidine

HRID 342508
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 342508
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][OH:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[H][H].Cl[C:19]1[C:24]([O:25][CH3:26])=[C:23]([CH2:27][O:28][CH3:29])[N:22]=[CH:21][N:20]=1>CN(C)C=O.ClCCl.O>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH2:11][CH2:12][O:13][C:19]2[C:24]([O:25][CH3:26])=[C:23]([CH2:27][O:28][CH3:29])[N:22]=[CH:21][N:20]=2)=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]
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Komponenten

7

Edukt 4

HCID 24758Sodium hydrideHCID 79410p-tert-Butylphenethyl alcoholHCID 152793504-Chloro-5-methoxy-6-(methoxymethyl)pyrimidineHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 678391484-[2-(4-Tert-butylphenyl)ethoxy]-5-methoxy-6-methoxymethylpyrimidineAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel
HCID 21908982Water methylene chlorideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

5.4 g (0.03 mol) of 2-(4-tert-butylphenyl)ethanol were added dropwise at 50° C. to a suspension of 1.2 g (0.03 mol) of sodium hydride (60% dispersion in oil) in 50 ml of dry dimethylformamide, and the mixture was stirred until the evolution of hydrogen had ceased. The mixture was cooled to 0° C., and 4.7 g (0.025 mol) of 4-chloro-5-methoxy-6-methoxymethylpyrimidine (Coll. Czechoslov. Chem. Commun. 33, 2266 (1968)) were added. The mixture was stirred for 1 hour at room temperature and for 2 hours at 100° C. After the solvent had been stripped off, the residue was taken up in dichloromethane/water, and the organic phase was dried and evaporated on a rotary evaporator. The crude product was chromatographed on silica gel using ethyl acetate. 3.8 g (46% of theory) of 4-[2-(4-tert-butylphenyl)ethoxy]-5 -methoxy-6 -methoxymethylpyrimidine were obtained in the form of a yellow oil.

Aufarbeitung

  1. customthe organic phase was dried
  2. customevaporated on a rotary evaporator
  3. customThe crude product was chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-5f15bb1b4b234011ac016c5a9a64901d
Quelldatensatz
uspto-grants-1999_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05859020

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