C[Si](C)(C)N[Si](C)(C)C.C([Li])CCC.CCCCCC.[C:21](#[N:23])[CH3:22].[CH:24]([CH:27]1[C:38](=[O:39])[C:30]2=[C:31]3[CH2:37][CH2:36][O:35][C:32]3=[N:33][CH:34]=[C:29]2[CH2:28]1)([CH3:26])[CH3:25]>O1CCCC1.[Cl-].[NH4+]>[OH:39][C:38]1([CH2:22][C:21]#[N:23])[C:30]2=[C:31]3[CH2:37][CH2:36][O:35][C:32]3=[N:33][CH:34]=[C:29]2[CH2:28][CH:27]1[CH:24]([CH3:26])[CH3:25]
To a solution of 1,1,1,3,3,3-hexamethyldisilazane (684 mg, 4.24 mmol) in tetrahydrofuran (3 mL) was added 1.6M butyllithium/hexane solution (2.65 mL, 4.24 mmol) at −78° C., and the mixture was stirred for 15 min. A solution of acetonitrile (234 μL, 4.45 mmol) in tetrahydrofuran (1 mL) was added thereto, and the mixture was stirred for 30 min. Then, a solution of 7-isopropyl-1,2,6,7-tetrahydro-8H-cyclopenta[d]furo[2,3-b]pyridin-8-one (460 mg, 2.12 mmol) in tetrahydrofuran (6 mL) was added. After stirring for 20 min, the reaction solution was diluted with saturated aqueous ammonium chloride solution, and the solvent was evaporated under reduced pressure. The residue was diluted with ethyl acetate, and the mixture was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=30/70→80/20) to give the title compound (457 mg, yield 83%).
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