Dimethylformamide → 2-[2-(2,5-Dimethylphenoxymethyl)-alpha-methoxybenzyl]pyridine

HRID 369118Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 369118
[CH3:1][C:2]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][C:3]=1[O:4][CH2:5][C:6]1[CH:19]=[CH:18][CH:17]=[CH:16][C:7]=1[CH:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)[OH:9].[CH3:25]N(C)C=O.CI.[H-].[Na+]>CCOCC>[CH3:1][C:2]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][C:3]=1[O:4][CH2:5][C:6]1[CH:19]=[CH:18][CH:17]=[CH:16][C:7]=1[CH:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)[O:9][CH3:25]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 155451342-[2-(2,5-Dimethylphenoxymethyl)-alpha-hydroxybenzyl]pyridine

Produkt 1

HCID 155451352-[2-(2,5-Dimethylphenoxymethyl)-alpha-methoxybenzyl]pyridineAusbeute 92,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a mixture of 0.42 g (1.3 mmol) of 2-[2-(2,5-dimethylphenoxymethyl)-α-hydroxybenzyl]pyridine, 4 ml of N,N-dimethylformamide and 0.12 ml (2 mmol) of methyl iodide was added 0.07 g (1.7 mmol) of 60% sodium hydride under ice-cooling and stirred at the same temperature for 3 hours. After completion of the reaction, 100 ml of ether was added and washed twice with 80 ml of brine. The ether layer was dried over anhydrous magnesium and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate/n-hexane) to give 2-[2-(2,5-dimethylphenoxymethyl)-α-methoxybenzyl]pyridine (0.40 g, 92.3%) as colorless oil.

Aufarbeitung

  1. temperaturecooling
  2. additionwas added
  3. washwashed twice with 80 ml of brine
  4. dry with materialThe ether layer was dried over anhydrous magnesium
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (ethyl acetate/n-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-12e9befd8bfc4c159ca9b3d7aae2a191
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06136837

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