[O:1]1[C:5]2([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]2)[CH2:4]C[C:2]1=[O:11].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([I:26])=[CH:22][CH:21]=1.C(#[N:29])C>C(OCC)(=O)C>[I:26][C:23]1[CH:24]=[CH:25][C:20]([CH2:19][N:29]2[CH2:4][C:5]3([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]3)[O:1][C:2]2=[O:11])=[CH:21][CH:22]=11-Oxa-spiro[4.5]decan-2-one (96 mg, 0.618 mmol), cesium carbonate (Cs2CO3) (605 mg, 1.855 mmol) and 1-bromomethyl-4-iodo-benzene (220 mg, 0.742 mmol) were mixed in acetonitrile (2.5 mL). The reaction mixture was heated at 70° C. for 5 hours, and the diluted with ethyl acetate (8 mL). The mixture was washed with water (2×4 mL) and brine (2×4 mL). The combined organic phase was dried over anhydrous sodium sulfate and concentrated. The crude residue was purified on silica gel eluting with 5 to 25% ethyl acetate in hexane to give the product as a white powder (112 mg, 49%). 1H NMR (300 MHz, CDCl3): δ 7.68 (dd, 2H), 7.03 (dd, 2H), 4.36 (s, 2H), 3.08 (s, 2H), 1.78 (m, 4H), 1.46 (m, 6H).
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