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0 °C

MS (m/z)=404 (M+H+). To a suspension of 0.35 g of triphenyl(quinolin-2-ylmethyl)phosphonium bromide in 5 mL of THF was added 3 mL of 0.5 M sodium methoxide at 0° C under Argon, followed by a solution of 6-Hydroxy-7,8-dimethyl-3,4-dihydrospiro[chromene-2,1′-cyclobutane]-5-carbaldehyde 0.18 g) in 10 mL of THF. The solution was stirred for 1 hr at 0° C., warmed to room temperature, and stirred for 2 hrs. The tetrahydrofuran was evaporated, and the residue was partitioned between EtOAc and H2O, washed with brine, then dried over Na2SO4. The crude material was purified on a silica column eluting with 1:8 EtOAc/Hexane. 50 mg of 7,8-dimethyl-5-[2-quinolin-2-ylvinyl] 3,4-dihydrospiro-[chromene-2,1′-cyclobutan]-6-ol which was precipitated with hexane. 1H-NMR (300 MHz, CDCl3) δ=1.70-1-76 (m, 3H), 1.78-1.97 (m, 5H), 2.09-2.30 (m, 8H), 2.81-2.85 (t, 2H), 5.70 (brs, 1H), 7.18-7.24 (d, 1H), 7.50-7.56 (m, 2H), 7.71-7.82 (m, 3H), 8.08-8.13 (m, 2H) ppm. 13C-NMR (75 MHz, CDCl3) δ=12.24, 12.34, 12.60, 21.25, 29.31, 34.10, 76.51, 117.47, 119.17, 119.65, 112.33, 126.29, 126.46, 127.45, 127.55, 129.23, 129.88, 130.01, 133.47, 136.49, 145.10, 155.55 ppm. MS (m/z)=372 (M+H+).

1. temperaturewarmed to room temperature
2. stirringstirred for 2 hrs
3. customThe tetrahydrofuran was evaporated
4. customthe residue was partitioned between EtOAc and H2O
5. washwashed with brine
6. dry with materialdried over Na2SO4
7. customThe crude material was purified on a silica column
8. washeluting with 1:8 EtOAc/Hexane
9. custom50 mg of 7,8-dimethyl-5-[2-quinolin-2-ylvinyl] 3,4-dihydrospiro-[chromene-2,1′-cyclobutan]-6-ol which was precipitated with hexane