Diisoamyl ketone → 2,8-Dimethyl-5-nonanol
Reaktionsgleichung
[CH3:1][CH:2]([CH2:4][CH2:5][C:6](=[O:12])[CH2:7][CH2:8][CH:9]([CH3:11])[CH3:10])[CH3:3].[BH4-].[Na+]>CO>[CH3:3][CH:2]([CH2:4][CH2:5][CH:6]([OH:12])[CH2:7][CH2:8][CH:9]([CH3:11])[CH3:10])[CH3:1]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A solution of 5.63 g (33 mmol) of 2,8-dimethylnonan-5-one in 150 ml of methanol was cooled to 0° C. and treated with 0.8 g (21 mmol) of sodium borohydride. After 1 h, the solution was quenched with 1N HCl; diluted with 1:1 hexane/ether; washed sequentially with 1N NaOH, water, and saturated brine; dried over MgSO4 ; and concentrated in vacuo. Flash chromatography using 10% ethyl acetate in hexane gave 2.30 g (40%) of the desired compound (Rf 0.36, 20% ethyl acetate in hexane) as a colorless oil. 1H NMR (CDCl3) 0.88 (d, J=7 Hz, 6H), 0.89 (d, J=7 Hz, 6H), 1.1-1.6 (m, 10H), 3.56 (m, 1H).