Lithium hydroxide, monohydrate → 3-Vinyl-tetrahydro-pyran-3-carboxylic acid

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Reaction Steps

A solution of 3-vinyl-tetrahydro-pyran-3-carboxylic acid benzyl ester (809.5 mg, 3.286 mmol) in tetrahydrofuran/methanol/water (25 mL, 2:2:1) was treated with lithium hydroxide monohydrate (413.6 mg, 9.859 mmol). After stirring at room temperature for 2 h, more lithium hydroxide monohydrate (413.6 mg 9.859 mmol) was added. After stirring at room temperature for 2 h, the volatiles were removed in vacuo and the residue was cooled to 0° C. and quenched with hydrochloric acid (1 M). The aqueous layer was saturated with sodium chloride, extracted with dichloromethane (3×). The combined organics were filtered through a phase separator and the volatiles were removed in vacuo. The residue was purified by silica gel chromatography using a 25 g Isolute cartridge eluted with a continuous gradient of iso-hexanes/ethyl acetate 1:0 to 1:1 to afford crude title compound which was dissolved in diethyl ether. Organics were extracted with a saturated solution of sodium bicarbonate. The aqueous layer was acidified with hydrochloric acid (2 M) to pH ˜2, saturated with sodium chloride and extracted with dichloromethane (2×) to provide the title compound (377.1 mg, 73%) as a white solid. 1H NMR (300 MHz, CDCl3) δ 1.59-1.90 (m, 3H), 2.27-2.38 (m, 1H), 3.39-3.55 (m, 2H), 3.87 (app dt, J=11.2, 4.0 Hz, 1H), 4.26 (dd, J=11.4, 2.0 Hz, 1H), 5.22-5.32 (m, 2H), 5.79 (dd, J=17.8, 10.7 Hz, 1H).

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