HCID 10967505, compound → HCID 23356039, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of isothiochroman from step 1 above (253 mg, 0.94 mmol) in 3 ml of CH3CN was added dropwise a solution of ceric ammonium nitrate (1.550 g, 283 mmol) in 3 ml of H2O. The reaction mixture was stirred at 0° C. for 10 minutes and then at room temperature for 10 minutes, followed by extraction with CH2Cl2 (10 ml×3). The combined organic layers were washed with brine and water, dried over MgSO4, and then concentrated to a yellow residue (213 mg, 0.89 mmol) in 95% yield, which was found to be pure by H1NMR. 1H NMR (300 MHz, CDCl3) d:2.90 (m, 2H, HCHa,eCHC=O), 3.56 (m, 2H, HCHae--S), 3.73 (s, 3H, OCH3), 3.74 (s, 3H, OCH3), 3.75 (m, 1H, HC--S), 6.75 (m, 2H, ArH). 13C NMR (75.44 MHz, CDCl3) δ:22.2, 26.0, 37.4, 52.8, 136.2, 137.0, 140.0, 140.5, 172.0 (CO ester), 185.8, 187.0 (CO quinones). IR: (neat) 2956, 1736, 1658, 1607, 1442, 1409 cm-1.

Provenance & Evidence