[F:1][C:2]1[C:3]([O:10][CH2:11][Si](C)(C)C)=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[F-].[Cs+]>CN(C=O)C.C([O-])(O)=O.[Na+]>[F:1][C:2]1[C:3]2[O:10][CH2:11][CH:5]([OH:6])[C:4]=2[CH:7]=[CH:8][CH:9]=1A mixture of 3-fluoro-2-((trimethylsilyl)methoxy)benzaldehyde (6.75 g, 29.8 mmol) and CsF (13.73 g, 90 mmol) in DMF (88 mL) were heated in 95° C. oil bath for 3 days. At the conclusion of this period, the reaction was analyzed by HPLC, which showed the starting material had disappeared. The reaction mixture was cooled to rt, diluted with aqueous NaHCO3 and extracted with Et2O (3×15 mL), followed by EtOAc (3×15 mL). The combined organic layers were washed with water (25 mL), brine (25 mL), dried (MgSO4), and concentrated to afford Compound 1B as a brown oil (4.6 g). The crude product was used in next step without further purification.
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