Dimethyl 2,2'-(1,3-dioxolane-2,2-diyl)diacetate → 2-(2-(2-Hydroxyethyl)-1,3-dioxolan-2-yl)ethan-1-ol
Reaktionsgleichung
[O:1]1[CH2:5][CH2:4][O:3][C:2]1([CH2:11][C:12](OC)=[O:13])[CH2:6][C:7](OC)=[O:8].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[O:1]1[CH2:5][CH2:4][O:3][C:2]1([CH2:6][CH2:7][OH:8])[CH2:11][CH2:12][OH:13]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a solution of 2.6 g (12 mmol) of dimethyl 2,2′-(1,3-dioxolane-2,2-diyl)diacetate in 100 mL of dry THF was added 1.4 g (36 mmol) of LAH at 0° C. The reaction mixture was then refluxed for 1 h, was quenched with 15% NaOH aqueous solution (3 mL) and water (3 mL). The mixture was stirred overnight, filtered through celite. The residue was washed twice with THF (100 mL×2). The combined organic phase was evaporated. Chromatography on silica gel afforded 1.3 g (8.0 mmol, yield: 66%) of 2,2′-(1,3-dioxolane-2,2-diyl)diethanol: MS (m/e): 163 (M+1)+.