Reaktion #9741

Reaktionsgleichung

Water

ethyl 3-[(benzylthio)methyl]-5-[4-(trifluoromethyl)phenyl]thiophene-2-carboxylate

intermediate 45

ethyl 3-[(benzylthio)methyl]-5-[4-(trifluoromethyl)phenyl]thiophene-2-carboxylate

lithium aluminium hydride

hydrochloric acid

→

title compound

{3-[(benzylthio)methyl]-5-[4-(trifluoromethyl)phenyl]thien-2-yl}methanol

Lösungsmittel

tetrahydrofuran

ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwith cooling for 3 hours
2. 2
   Extraktionthe further water (50 ml), the resulting mixture was extracted twice with ethyl acetate
3. 3
   Trocknendried over magnesium sulfate
4. 4
   Einengenconcentrated
5. 5
   SonstigeThe residue was purified by SPE (Si cartridge)
6. 6
   Wascheneluting initially with cyclohexane:chloroform (1:1)

Vorschrift

A solution of ethyl 3-[(benzylthio)methyl]-5-[4-(trifluoromethyl)phenyl]thiophene-2-carboxylate (intermediate 45, 0.87 g) in dry tetrahydrofuran (5 ml) was cooled to 0° C. and 1M lithium aluminium hydride solution in diethyl, ether (0.299 ml) added. The reaction mixture as stirred with cooling for 3 hours. Water (0.5 ml) was added drop-wise followed by 2M hydrochloric acid (0.5 ml), the further water (50 ml), the resulting mixture was extracted twice with ethyl acetate, the extracts were combined, dried over magnesium sulfate and concentrated. The residue was purified by SPE (Si cartridge) eluting initially with cyclohexane:chloroform (1:1) and then chloroform to give the title compound as a white solid.

Quelle