Water → 1,4-Dioxaspiro[4.5]decan-6-ylmethanol

関与物質

反応手順

To a mixture of methyl 1,4-dioxaspiro[4.5]decane-6-carboxylate (3.00 g, 15.0 mmol) in THF (45 mL) at 0° C. was added LiAlH4 (2M in TI-IF (9.00 mL, 18.0 mmol) dropwise. The mixture was then allowed to warm to rt and stirred overnight. The mixture was then cooled to 0° C. and 1.36 mL of H2O was added very slowly. The reaction mixture was basified by adding 0.682 mL of 15% NaOH and then 3.41 mL of H2O. The resulting mixture was filtered through a pad of celite, washed with Et2O, and concentrated. The residue was purified by column chromatography to give the title compound. 1H NMR (500 MHz, CDCl3) δ 3.95-4.05 (m, 4H), 3.71-3.79 (m, 1H), 3.52-3.59 (m, 1H), 2.81 (dd, 1H, J=3.9 Hz, 7.1 Hz), 1.78-1.91 (m, 2H), 1.61-1.73 (m, 3H), 1.41-1.53 (m, 2H), 1.24-1.40 (m, 2H).

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