Pyruvic Acid → 2,2-Diethoxypropionic acid

To a stirred solution of pyruvic acid (14 mL, 0.2 mol) and triethylorthoformate (80 mL) at 10° C. was added concentrated sulfuric acid (1 mL). The resulting mixture was stirred at 5–10° C. for 1 h and then diluted with dichloromethane (200 mL). The organic solution was washed successively with water (3×80 mL) and saturated sodium chloride solution (80 mL) and then dried over anhydrous sodium sulfate. The mixture was filtered and then concentrated to give a quantitative yield of 2,2-diethoxypropionic acid as an oil. 1H NMR (CDCl3, 400 MHz): δ 1.30 (t, 6H), 1.61 (s, 3H), 3.57 (q, 4H), 8.62 (s, 1H). The acid form was quantitatively converted to its cesium salt (25) by dissolving the acid in water (25 mL) followed by treatment with an equimolar quantity of cesium carbonate, and then lyophilization. 1H NMR (D2O, 400 MHz): δ 0.98 (t, 6H), 1.28 (s, 3H), 3.22 (q, 2H), 3.47 (q, 2H).

1. washThe organic solution was washed successively with water (3×80 mL) and saturated sodium chloride solution (80 mL)
2. dry with materialdried over anhydrous sodium sulfate
3. filtrationThe mixture was filtered
4. concentrationconcentrated

ORD-Eintrag

ord-4d926a85fc384c1385107c1f6e102a72

Quelldatensatz

uspto-grants-2007_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07232924B2