Cl[CH2:2][C@:3]([C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][C:9]=1[F:15])([OH:7])[C@H:4]([OH:6])[CH3:5].C[O-].[Na+].O>CO>[O:7]1[C@:3]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][C:9]=2[F:15])([C@H:4]([OH:6])[CH3:5])[CH2:2]1A solution of 1.00 g (4.23 mmol) of (2R,3R)-1-chloro-2-(2,4-difluorophenyl)butane-2,3-diol in 8 mL of methanol was cooled in ice, and 0.91 g (4.65 mmol) of a 28% solution of NaOMe in methanol was added thereto. The reaction was performed for 2 hours, and 10 mL of water was added to stop the reaction. Then, extraction was performed with 20 mL of ethyl acetate. After drying over anhydrous sodium sulfate, concentration was performed under reduced pressure to obtain a crude product. The product was quantitatively analyzed by HPLC (under the same HPLC measurement conditions as those in Example 10). The title compound was obtained in a yield of 97%. 1H-NMR (400 MHz, CDCl3) δ: 1.19 (d, 3H, J=6.3 Hz), 2.22 (s, 1H), 2.91 (d, 1H, J=4.9 Hz), 3.28 (d, 1H, J=4.9 Hz), 4.11 (d, 1H, J=6.3 Hz), 6.80-6.91 (m, 2H), 7.34-7.39 (m, 1H).
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