Pyridine → 2-Benzyl-4-(chloromethyl)furan

HRID 1448958

Reaktionsgleichung

Reaktionsgleichung von HRID 1448958
S(Cl)([Cl:3])=O.N1C=CC=CC=1.[CH2:11]([C:18]1[O:19][CH:20]=[C:21]([CH2:23]O)[CH:22]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1(C)C=CC=CC=1>[CH2:11]([C:18]1[O:19][CH:20]=[C:21]([CH2:23][Cl:3])[CH:22]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 123643963-Furanmethanol, 5-(phenylmethyl)-

Produkt 1

HCID 127908922-Benzyl-4-(chloromethyl)furan

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A solution of 13 g of thionyl chloride in toluene was added dropwise over 15 minutes to a mixture of 15.8 g pyridine and 18.8 g 2-benzyl-4-hydroxymethylfuran, in toluene, at a temperature of 0°-5° C. The mixture was slowly warmed to 80° C. and stirred for 11/2 hours and then cooled in an ice-bath, poured into ice and filtered. The resulting solution was extracted with diethyl ether, washed with water and then with sodium bicarbonate solution, and dried over magnesium sulphate. The solution was then stripped of solvent, yielding a brown oil, which was chromatographed over silica gel using toluene as eluent to give 2-benzyl-4-chloromethylfuran (1A) as a brown oil.

Aufarbeitung

  1. temperaturecooled in an ice-bath
  2. additionpoured into ice
  3. filtrationfiltered
  4. extractionThe resulting solution was extracted with diethyl ether
  5. washwashed with water
  6. dry with materialwith sodium bicarbonate solution, and dried over magnesium sulphate
  7. customyielding a brown oil, which
  8. customwas chromatographed over silica gel

Quellen und Nachweise

ORD-Eintrag
ord-54b29a6b27614b24a45f9a624ead9360
Quelldatensatz
uspto-grants-1980_02
Patentnummer
US04188400

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