[Si:1]([O:8][C:9]1[C:10]([F:16])=[C:11](O)[CH:12]=[CH:13][CH:14]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C([Li])(CC)C.[C:22](=[O:24])=[O:23].C(OCC)C.O>C1COCC1>[Si:1]([O:8][C:9]1[C:10]([F:16])=[C:11]([CH:12]=[CH:13][CH:14]=1)[C:22]([OH:24])=[O:23])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]A solution of 3-tert-butyldimethylsilyloxy-2-fluorophenol (10.59 g, 46.8 mmol) in THF (150 ml) cooled to -70° C. was added dropwise over 5 min. sec-butyllithium (42 ml, 1.12M in cyclohexane). The reaction mixture was stirred ad -70° C. for 1 h and then poured into a slurry of dry-ice/diethyl ether. Water (200 ml) was added cautiously and the organic layer separated and discarded. The aqueous layer was acidified to pH 2 with concentrated HCl and extracted with ethyl acetate (3×100 ml). The combined organic extracts were dried (MgSO4) and evaporated to afford title compound (7.90 g, 70%) as a white solid.
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