Hydrochloric Acid → (2-Benzylthiazol-4-yl)methanol

HRID 615920

Reaktionsgleichung

Reaktionsgleichung von HRID 615920
[CH2:1]([C:8]1[S:9][CH:10]=[C:11]([C:13](OCC)=[O:14])[N:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.CCOCC.O>C1(C)C=CC=CC=1>[CH2:1]([C:8]1[S:9][CH:10]=[C:11]([CH2:13][OH:14])[N:12]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3283Diethyl EtherHCID 1491568Ethyl 2-benzylthiazole-4-carboxylate

Produkt 1

HCID 13102618(2-Benzylthiazol-4-yl)methanolAusbeute 81,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Reaktionsbedingungen

Temperatur
-5 °C

Versuchsvorschrift

90 ml of a toluene solution of 2M/liter of diethyl sodium aluminum dihydride were added dropwise at -10° C. to a solution of 20 g of the product of Step A in 100 ml of toluene and the mixture was stirred at -5° C. for one hour. 150 ml of aqueous 2N hydrochloric acid were added dropwise to the mixture at -20° C. and then ether and water were added thereto. The mixture was filtered and the organic phase of the filtrate was washed with water, dried and evaporated to dryness. The residue was chromatographed over silica gel and was eluted with a 7-3 methylene chloride-ethyl acetate mixture to obtain 13.6 g of (2-benzyl-4-thiazolyl)-methanol melting about 50° C.

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. washthe organic phase of the filtrate was washed with water
  3. customdried
  4. customevaporated to dryness
  5. customThe residue was chromatographed over silica gel
  6. washwas eluted with a 7-3 methylene chloride-ethyl acetate mixture

Quellen und Nachweise

ORD-Eintrag
ord-d91495a89de14125bee051b1489ed2b0
Quelldatensatz
uspto-grants-1985_02
Patentnummer
US04501894

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