反应详情

To a 0° C. solution of ethyl [trans-4-(hydroxymethyl)cyclohexyl]acetate (102. 8 mg, 0.514 mmol) in CH2Cl2 (6 n-L) was added Dess-Martin periodinane. The reaction was warmed to room temperature and stirred for several hours. The reaction was then diluted with EtOAc (50 mL) and washed with 1N NaOH and brine (15 mL each). The organic layer was dried over Na2SO4, filtered, and concentrated. Purification of the residue by flash chromatography on silica gel (5 to 25% EtOAc/hexanes) afforded ethyl (trans-4-formylcyclohexyl)acetate. Rf=0.57 (40% EtOAc/hexanes). 1H NMR (CDCl3, 500 MHz) δ 9.61 (d, J=1.4 Hz, 1H), 4.13 (q, J=7.1 Hz, 2H), 2.13-2.22 (m, 3H), 1.98-2.01 (m, 2H), 1.87-1.91 (m, 2H), 1.77 (m, 1H), 1.31 (qd, J=13.0, 3.4 Hz, 2H), 1.25 (t, J=7.1 Hz, 3H), 1.05 (qd, J=13.0, 3.4 Hz, 2H).

1. washwashed with 1N NaOH and brine (15 mL each)
2. dry with materialThe organic layer was dried over Na2SO4
3. filtrationfiltered
4. concentrationconcentrated
5. customPurification of the residue by flash chromatography on silica gel (5 to 25% EtOAc/hexanes)