Lithium borohydride → 2-Thiophenemethanol, 5-[4-(trifluoromethyl)phenyl]-
Reaktionsgleichung
C[C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=2)[S:4][C:3]=1[CH:17]=[O:18].[Li+].[BH4-]>C1COCC1>[F:15][C:13]([F:14])([F:16])[C:10]1[CH:9]=[CH:8][C:7]([C:5]2[S:4][C:3]([CH2:17][OH:18])=[CH:2][CH:6]=2)=[CH:12][CH:11]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a solution of 3-methyl-5-(4-Trifluoromethyl-phenyl)-thiophene-2-carbaldehyde (0.140 g, 0.518 mmole) in THF (5 mL), is added to LiBH4 (0.056 g, 2.57 mmole) in one portion at 0° C. The reaction is kept at 0° C. for 15 minutes and warmed up to room temperature for 1 hour. The reaction is quenched using 1N HCl (10 mL) at 0° C. The THF is removed on rota vapor, the aqueous solution is then extracted with ethyl acetate (2×10 mL). The combined organic solution is washed with brine (3×20 mL), dried over Na2SO4 and concentrated. The crude product is purified on a silica gel column, eluting with 20% ethyl acetate in hexane and concentrated to provide the titled compound as white solid.