Water → HCID 13367668, Verbindung

HRID 1583594Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1583594
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH2:9][OH:10])=[CH:7][CH:6]=1.[F:13][CH2:14][CH2:15][O:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21]Cl)=[CH:19][CH:18]=1.O>C(#N)C>[CH3:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH2:9][O:10][CH2:21][C:20]2[CH:19]=[CH:18][C:17]([O:16][CH2:15][CH2:14][F:13])=[CH:24][CH:23]=2)=[CH:7][CH:6]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 77384-Methoxybenzyl alcoholHCID 24758Sodium hydrideHCID 202592671-(Chloromethyl)-4-(2-fluoroethoxy)benzene

Produkt 1

HCID 13367668HCID 13367668, VerbindungAusbeute 69,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Sodium hydride (0.32 g; 60% in oil) was suspended in 30 ml of dry acetonitrile, and 1.1 g of 4-methoxybenzyl alcohol was added. The mixture was stirred at 50° to 60° C. for 30 minutes. Then, 1.5 g of 4-(2-fluoroethoxy)benzyl chloride was added. The mixture was heated under reflux for 3 hours. The reaction mixture was cooled to room temperature, poured into water, and extracted with toluene. The toluene layer was washed with water, and dried over anhydrous sodium sulfate. Toluene was evaporated under reduced pressure. The resulting crude ether was purified by silica gel (50 g) column chromatography (developing solvent: a 9:1 mixture of benzene and ethyl acetate) to give 1.6 g of 4-(2-fluoroethoxy)benzyl 4-methoxybenzyl ether.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. extractionextracted with toluene
  4. washThe toluene layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customToluene was evaporated under reduced pressure
  7. customThe resulting crude ether was purified by silica gel (50 g) column chromatography (
  8. additiona 9:1 mixture of benzene and ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-fc5ec1d0223d4612953cb98b8948e1c7
Quelldatensatz
uspto-grants-1985_11
Patentnummer
US04552894

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