[CH3:1][O:2][CH:3]([O:16][CH3:17])[CH2:4][CH:5]([C:11](OCC)=[O:12])[C:6](OCC)=[O:7].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>CCOCC>[CH3:17][O:16][CH:3]([O:2][CH3:1])[CH2:4][CH:5]([CH2:11][OH:12])[CH2:6][OH:7]
Diethyl (2,2-dimethoxyethyl)malonate (115.0 g, 0.46 mol) was added to a suspension of lithium aluminum hydride (38.0 g, 1.00 mol) in 400 ml of dry ether at a rate to maintain a gentle reflux. After stirring for 15 min. 40 ml of water, 40 ml of 15% aqueous NaOH, and 120 ml of water were added and stirring was continued until a white suspension was obtained. The inorganic salts were filtered off and extracted with several 200 ml portions of tetrahydrofuran (THF). The combined organic extracts were evaporated and distilled twice in vacuum to yield 50.23 g (66.5%) of the title compound. B.p. 116°-125° (0.02 mm Hg).
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