反应详情

NaH (60% in mineral oil dispersion, 6 mmol, 1.2 equiv.) was added to a stirred solution of aldehyde 8 (5 mmol, 1 equiv.) in anhydrous dimethylsulfoxide (DMSO) at room temperature. After 1 h of stirring at the same temperature, 1-bromooctane was added and the mixture stirred for another 3 h. Distilled water was added to the reaction mixture which was then extracted with CH2Cl2. The organic layer was washed with brine, dried (anhydrous Na2SO4) and evaporated under reduced pressure. The residue was purified by column chromatography with EtOAc/hexane as eluting solvents as described in Section 5.4.1. Yield: 62%; 1 H NMR (300 MHz, CDCl3): δ 9.98 (s, 1 H), 8.53 (s, 1 H), 7.66 (s, 1 H), 7.57-7.46 (m, 3 H), 7.39-7.29 (m, 2 H), 7.13 (d, J=7.2H, 1 H), 4.1 (t, J=8.7 Hz, 2 H), 2.42 (s, 3 H), 1.86 (t, J=3 H), 1.29-1.24 (m, 10 H), 0.86 (t, J=6.6 Hz, 3 H); 13C NMR (75 MHz, CDCl3): δ 184.8, 143.7, 141.6, 138.9, 135.4, 135.1, 129.1, 128.9, 127.1, 119.3, 119.2, 118.5, 116.8, 111.6, 47.4, 32.7, 31.6, 29.6, 29.0, 26.7, 22.5, 14.0.

1. additionwas added
2. extractionwas then extracted with CH2Cl2
3. washThe organic layer was washed with brine
4. dry with materialdried (anhydrous Na2SO4)
5. customevaporated under reduced pressure
6. customThe residue was purified by column chromatography with EtOAc/hexane
7. washas eluting solvents