Ethanol → HCID 66579331, compound

Participants

Reaction Steps

To a mixture of methyl (2E)-4-(1,4,8-trioxaspiro[4.5]dec-6-yl)but-2-enoate (0.747 g, 3.08 mmol) in THF (9 mL) was added anhydrous LiCl (0.261 g, 6.71 mmol) and Sodium borohydride (0.233 g, 6.17 mmol). EtOH (12 mL) was then added slowly and the mixture was stirred at rt overnight. It was cooled to 0° C. and quenched with 10% aqueous citric acid. The organic layer was then concentrated and the mixture was diluted with water and CH2Cl2. Extracted 3× with CH2Cl2. The combined organics were dried (anhd. Na2SO4), filtered, and concentrated. The residue was purified by column chromatography to give the title compound. 1H NMR (500 MHz, CDCl3) δ 3.91-4.05 (m, 4H), 3.77-3.90 (m, 2H), 3.60-3.70 (m, 3H), 3.44 (dd, 1H, J=8.8 Hz, 11.0 Hz), 1.14-1.82 (m, 9H).

Provenance & Evidence