Trifluoroacetic acid → 2-(Diethoxy-phosphoryl)-4-phenyl-butyric acid

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Reaction Steps

Trifluoroacetic acid (4 mL) was added drop wise to a stirring solution of 2-(diethoxy-phosphoryl)-4-phenyl-butyric acid tert-butyl ester (1.00 g, 2.81 mmol) in anhydrous dichloromethane (16 ml). The mixture was stirred for 2 hours at room temperature followed by the removal of the solvent. The crude residue was purified by flash chromatography (100% dichloromethane-2.5% methanol in dichloromethane) to afford the desired compound as a yellowish oil. 1H NMR (CDCl3, 400 MHz) δ 11.21 (br s, 1H), 7.29-7.14 (m, 5H), 4.24-4.12 (m, 4H), 3.09-3.00 (m, 1H), 2.82-2.75 (m, 1H), 2.64-2.57 (m, 1H), 2.35-2.27 (m, 1H), 2.15-2.11 (m, 1H), 1.31-1.25 (m, 6H); 13C (CDCl3, 100 MHz) δ 170.4, 140.4, 128.4, 128.3, 126.1, 63.4, 63.2, 45.1, 43.8, 34.0, 28.5, 16.0; 31P (CDCl3, 400 MHz) δ 24.3; HRMS calcd. for C14H21O5P 300.1127, found 300.1129.

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