C(O[CH:5]([C:11]1[C:19]2[O:18][CH:17]=[CH:16][C:15]=2[CH:14]=[C:13]([F:20])[CH:12]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=O)C.CN(C)P(N(C)C)(N(C)C)=O.CO.O1CCCC1.[I-].[Sm+2].[I-]>C(OCC)(=O)C>[F:20][C:13]1[CH:12]=[C:11]([CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])[C:19]2[O:18][CH:17]=[CH:16][C:15]=2[CH:14]=1A mixture of 1.43 gm (5.10 mMol) ethyl 2-acetoxy-2-(5-fluorobenzofur-7-yl)acetate, 7.31 gm (40.8 mMol) hexamethylphosphoramide, 0.20 gm (6.12 mMol) methanol, and 153 mL (15.3 mMol) samarium(II) iodide tetrahydrofuran complex (0.1 M in tetrahydrofuran) was stirred at room temperature under a nitrogen atmosphere for 15 minutes. The reaction mixture was then diluted 10 fold with ethyl acetate, washed with water, and concentrated under reduced pressure to provide 1.09 gm (96%) of the desired compound.
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