[S:1]1[CH2:6][CH2:5][CH2:4][S:3][CH:2]1[C:7]#[N:8].[CH:9]([N-]C(C)C)(C)C.[Li+].C(NC(C)C)(C)C.C([Li])CCC.[CH2:29]([O:31][C:32](=[O:37])[CH:33]=[CH:34][CH2:35][F:36])[CH3:30].CI.[Cl-].[NH4+]>O1CCCC1>[CH2:29]([O:31][C:32](=[O:37])[CH:33]([CH3:9])[CH:34]([C:2]1([C:7]#[N:8])[S:3][CH2:4][CH2:5][CH2:6][S:1]1)[CH2:35][F:36])[CH3:30]
A solution of 1.45 g (10 mMole) of 1,3-dithian-2-carbonitrile in 10 ml of tetrahydrofuran is added to lithium diisopropylamide, prepared from diisopropylamine (1.01 g, 10 mMole) and butyllithium (4.8 ml of a 2.1 M solution, 10 mM) in 20 ml of tetrahydrofuran at -70° C. To the solution is added 1.25 g (9,5 mMole) of 3-monofluoromethylacrylic acid ethyl ester in 5 ml of tetrahydrofuran and the reaction mixture is stirredat -70° C. for 30 minutes after which 1.3 g (10 mMole) of methyl iodide is added and the mixture is maintained at 0° C. for 15 hours, then poured into aqueous ammonium chloride and extracted with ether. The ether solution is dried and evaporated to give the title compound.
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