反应详情

Dess-Martin periodinane (1.02 g, 2.4 mmol) was diluted in anhydrous CH2Cl2 (25 mL) under argon, and when solution was affected, 4-chlorophenethyl alcohol (33, 0.313 g, 2 mmol) was added dropwise. The mixture was stirred for 2 h and 15 min at room temperature, and was then quenched by addition of 20 mL sat. aq. Na2S2O3. After stirring at room temperature for 15 min, the layers were separated, and the aqueous layer was extracted with CH2Cl2 (2×50 mL). The organic layer was washed with H2O and sat. aq. NaCl (50 mL each) and was dried over anhydrous sodium sulfate and concentrated. The resulting semisolid residue was triturated with 10% EtOAc in hexanes, and the solid was filtered and discarded. The filtrate was concentrated, and the oily residue was purified by flash column chromatography (SiO2), eluting with a gradient of hexanes to 15% EtOAc in hexanes to afford the title compound as a clear yellow volatile oil (0.211 g, 88%). 1H-NMR (500 MHz; CDCl3): δ 9.75 (t, J=2.1 Hz, 1 H), 7.34 (d, J=8.3 Hz, 2 H), 7.15 (d, J=8.2 Hz, 2 H), 3.69 (d, J=2.0 Hz, 2 H).

1. customwas then quenched by addition of 20 mL sat. aq. Na2S2O3
2. stirringAfter stirring at room temperature for 15 min
3. customthe layers were separated
4. extractionthe aqueous layer was extracted with CH2Cl2 (2×50 mL)
5. washThe organic layer was washed with H2O and sat. aq. NaCl (50 mL each)
6. dry with materialwas dried over anhydrous sodium sulfate
7. concentrationconcentrated
8. customThe resulting semisolid residue was triturated with 10% EtOAc in hexanes
9. filtrationthe solid was filtered
10. concentrationThe filtrate was concentrated
11. customthe oily residue was purified by flash column chromatography (SiO2)
12. washeluting with a gradient of hexanes to 15% EtOAc in hexanes