6-(2-Cyclopentyl-2-hydroxy-but-3-ynyl)-2,2-dimethyl-[1,3]dioxin-4-one → {4-[3-cyclopentyl-4-(2,2-dimethyl-4-oxo-4H-1,3-dioxin-6-yl)but-1-ynyl]-2-ethylphenoxy}acetonitrile

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To a solution (4-bromo-2-ethylphenoxy)acetonitrile (1.99 g, 8.33 mmol) in diisopropylamine (9 mL) and DMF (3 mL) was added 6-(2-cyclopentyl-2-hydroxybut-3-ynyl)-2,2-dimethyl-4H-1,3-dioxin-4-one (2.00 g, 7.57 mmol), PdCl2(PPh3)2 (211 mg, 4 mol %), CuI (115 mg, 8 mol %). The mixture was heated to 90° C. for 30 min before it was cooled down to room temperature. The reaction was diluted with aqueous NH4Cl, extracted with EtOAc (3×50 mL). The combined organic extracts were washed with brine, dried with Na2SO4 and evaporated to dryness. The mixture was purified by flash column chromatography (10–50% EtOAc in hexanes) to give the product (1.9 g). 1H NMR (300 MHz, CDCl3) δ: 1.23 (t, J=12.07 Hz, 3H) 1.35–1.80 (m, 14H), 2.30 (m, 1H), 3.50 (m, 5 H), 4.62 (s, 2 H), 4.87 (s, 1 H), 6.90 (d, J=2.54 Hz, 1 H), 7.14 (m, 1 H), 7.38 (m, 1 H).

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