HCID 15612083, compound → HCID 14442084, compound

Participants

Reaction Steps

To a 0° C. solution of Example 8 Part A sulfide (500 mg, 1.11 mmol) in acetone (6 ml) was added, dropwise, freshly prepared Jones reagent (2.67M, ca. 1.2 ml). After stirring for 40 minutes, the reaction was quenched with 2-propanol and then concentrated in vacuo. The residue was then stirred with water (50 ml) for 30 minutes at which time a yellow solid had formed. The solid was collected by filtration, washed with water and air dried. Chromatography (flash, silica, 25 mm dia., ethyl acetate then 20% methanol/chloroform) provided a white solid. The solid was then triturated with 2 portions of hot ethyl acetate (ca. 10 ml each) leaving the desired sulfoxide as white amorphous solid: 1H NMR (tetradeuteriomethanol, 270 MHz) δ 7.53-7.62 (m, 4H), 7.02-7.19 (m, 4H), 3.46 (s, 2H), 2.55-2.95 (m, 4H), 1.75-2.00 (m, 2H); 13C NMR (tetradeuteriomethanol), 67.88 MHz, complete decoupling) δ 178.3, 142.4, 139.9, 138.3, 134.9, 130.6, 130.5, 129.4, 127.0, 56.4, 43.1.

Provenance & Evidence