Ethyl 8-methyl-1,4-dioxaspiro[4.5]decane-8-carboxylate → (8-Methyl-1,4-dioxaspiro(4.5)decan-8-yl)methanol

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Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere, lithium aluminum hydride (31.2 mmol, 1.25 g, 2.43 eq.) was added to a stirred solution of 3(12.84 mmol, 2.93 g) in anhydrous ethyl ether (275 mL) cooled to 0° C. in an ice bath. The resulting mixture was stirred at room temperature for 1.5 hours. In order to quench remaining lithium aluminum hydride, water (2.48 mL) followed by 40% aqueous sodium hydroxide solution (1.68 mL) and additional water (3.47 mL) were successively added with stirring to the reaction mixture. The insoluble precipitate was then removed by decanting and filtration. The filtrate was dried over magnesium sulfate, filtered, and concentrated in vacuo to give 4 (12.75 mmol, 2.28 g, 99%) as a yellow oil that was used in the next reaction without further purification: 1H NMR (CDCl3) δ 3.94 (4H, s), 3.39 (2H, s), 1.68-1.35 (8H, m), 0.96 (3H, s); 13C NMR (CDCl3) δ 109.3, 71.8, 64.4, 34.5, 31.5, 30.7, 21.3.

Provenance & Evidence