[H-].[Na+].[CH:3](OCC)=[O:4].[CH3:8][O:9][C:10]1[CH:19]=[CH:18][C:17]([F:20])=[C:16]2[C:11]=1[CH2:12][CH2:13][CH2:14][C:15]2=[O:21].Cl>C1COCC1.O.CO>[F:20][C:17]1[CH:18]=[CH:19][C:10]([O:9][CH3:8])=[C:11]2[C:16]=1[C:15](=[O:21])[CH:14]([CH:3]=[O:4])[CH2:13][CH2:12]2
Sodium hydride (12.7 g) (50% dispersion, washed with hexane) was suspended in dry THF under nitrogen. Ethyl formate (27 g) was added and the mixture was stirred for 20 minutes in an ice/water bath. 5-Methoxy-8-fluoro-1-tetralone (J. Med. Chem. (1973) 1003) (17 g) dissolved in THF was added and the mixture was allowed to warm to room temperature. The mixture was stirred under nitrogen for 24 hours. Methanol was added followed by water. The mixture was poured into water, acidified with conc. HCl (aq) and extracted into CHCl3. The organic phase was dried (MgSO4), filtered and concentrated to give a dark oil (22 g) which solidified on standing. This material was recrystallised from ethyl acetate/hexane to give the above compound, m.p. 66°-68° C.
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