[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([CH2:11][C:12](OCC)=[O:13])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[AlH4-].[Li+].O.[OH-].[Na+]>CCOCC>[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([CH2:11][CH2:12][OH:13])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1Ethyl 1,4-dioxaspiro[4.5]dec-8-ylacetate (3.40 g, 0.0149 mol) prepared according to the procedure of Itagaki, Noriaki; Kimura, Mari; Sugahara, Tsutomu; Iwabuchi, Yoshiharu. (Organic Letters 2005; 7 (19); 4181-4183.) was dissolved in ether (30.00 mL) and the mixture was cooled to 0° C. To the reaction was added 1.00 M lithium tetrahydroaluminate in ether (15.0 mL) and the resulting mixture was stirred at 0° C. for 60 minutes and at 25° C. for 2 hours. The reaction was cooled and water (0.40 mL, 0.022 mol) was added, followed by 1.00 M sodium hydroxide (0.40 mL). To the reaction was then added ether (100.00 mL) and the solid that precipitated was filtered off. The filtrate was concentrated using a rotary evaporator to give the product. 1H NMR(CDCl3): 3.94 (s, 4H), 3.67 (t, 2H), 1.20-1.80 (m, 11H).
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