HCID 23356090, compound → HCID 23356091, compound

Participants

Reaction Steps

To a stirred solution of 1.0 g (3.7 mmol) of the chloroiso-chroman from step 6 in 20 ml of acetonitrile was added dropwise a solution containing 6.25 g (11.4 mmol) of ceric ammonium nitrate in 20 ml of water. The mixture was stirred overnight and then diluted with 50 ml of CH2Cl2. The organic layer was separated and the aqueous phase was extracted twice with 25 ml CH2Cl2. The combined organic layer was washed once with 50 ml H2O, 50 ml brine and then dried over Na2SO4. After evaporation of solvents, flash chromatography of the residue with a solvent gradient of 5 to 20% ethyl acetate in toluene yielded 495 mg (55%) of the titled compound. (MP: 83.5° C.) 1H NMR (200 MHz, CDCl3) δ: 1.27 (t, 3H, J=7.1 Hz, CH3), 2.58 (ddt, 1H, J=19.0, 8.8, 3.2 Hz, HCHaCHC=O), 2.83 (d multiplets, 1H, HCHeCHC=O), 4.17 (dd, 1H, J=8.7, 3.3 Hz, OCHC=O), 4.20 (q, 2H, J=7.0 Hz, OCH2), 4.44 (dt, 1H, J=18.8, 3.4 Hz, HCHaO), 4.78 (d multipier, 1H, J=18.8, 2.6, 1.7 Hz, HCHeO), 6.95 (s, 1H, C=CH).

Provenance & Evidence