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The above oil was dissolved in 100 mL acetonitrile, and treated with 3.57 mL (30 mmol) benzyl bromide and 5.53 g (40 mmol) potassium carbonate, then refluxed 14 hours. Thin layer chromatography (TLC) showed a major spot at Rf=0.3 in 10% methylene chloride/hexane (with benzyl bromide at Rf=0.4). The reaction was cooled, poured into dilute aqueous hydrochloric acid/ethyl acetate, and the organic layer separated, washed with water and brine, dried over sodium sulfate, and evaporated. The residue was chromatographed on silica gel using methylene chloride/hexane as eluant to afford 4.0 g (63%) of an oil. 1H-NMR (δ, CDCl3): 1.77 (m, 4H), 2.75 (m, 4H), 5.045 (s, 2H), 6.62 (d, J=9, 1H), 7.3-7.5 (m, 6H); 13C-NMR (δ, CDCl3): 22.2, 22.9, 24.0, 30.7, 69.9, 109.8, 116.7, 127.1, 127.9, 128.6, 129.1, 129.3, 137.2, 137.5, 155.6.

1. temperaturerefluxed 14 hours
2. temperatureThe reaction was cooled
3. customthe organic layer separated
4. washwashed with water and brine
5. dry with materialdried over sodium sulfate
6. customevaporated
7. customThe residue was chromatographed on silica gel