O.[OH-].[Li+].C([O:6][C:7]([C:9]1([CH:19]=[CH2:20])[CH2:14][O:13][C:12]([CH2:17][F:18])([CH2:15][F:16])[O:11][CH2:10]1)=[O:8])C.Cl.[Cl-].[Na+]>O.O1CCCC1.CO>[F:16][CH2:15][C:12]1([CH2:17][F:18])[O:11][CH2:10][C:9]([CH:19]=[CH2:20])([C:7]([OH:8])=[O:6])[CH2:14][O:13]1
A solution of lithium hydroxide monohydrate (311 mg, 7.42 mmol) in water (8 mL) was added to a stirred solution of 2,2-bis-fluoromethyl-5-vinyl-[1,3]dioxane-5-carboxylic acid ethyl ester (619 mg, 2.47 mmol) in tetrahydrofuran/methanol (12 mL, 4:1). The reaction mixture was stirred at room temperature for 1 h and then cooled to 0° C. before acidifying to pH 4 with hydrochloric acid (1 M). The mixture was saturated with sodium chloride and then extracted with dichloromethane (3×10 mL). The extract was filtered through a hydrophobic frit and evaporated to give the title product (390 mg, 71%) as a colorless gum. 1H NMR (300 MHz, CDCl3) δ 4.00 (d, J=12.0 Hz, 2H), 4.35-4.73 (m, 6H), 5.30-5.43 (m, 2H), 5.68-5.81 (m, 1H).
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