Hydrogen Peroxide → HCID 86686450, compound

Participants

Reaction Steps

To a solution of 4-(methylthio)-1-(pentan-2-yl)-1H-indol-5-yltrifluoromethanesulfonate (13) (1.3 g, 3.4 mmol) in acetic acid (CH3COOH, 5.0 mL) at around 5° C. was added hydrogen peroxide (H2O2, 30%, 0.42 ml, 3.7 mmol). The mixture was allowed to warm to room temperature, stirred overnight, and then concentrated to dryness in vacuo to give 4-(methylsulfinyl)-1-(pentan-2-yl)-1H-indol-5-yl trifluoromethanesulfonate (17) (1.32 g, 100%). 1H NMR (500 MHz, CD2Cl2): δ 7.58 (d, J=9.0, 1H), 7.45 (d, J=2.5 Hz, 1H), 7.35 (m, 1H), 7.13 (d, J=9.0, 1H), 4.57 (m, 1H), 3.07 (d, 3H), 1.87 (m, 2H), 1.55 (m, 3H), 1.26 (m, 2H), 0.92 (m, 3H). Mass (ESI, M+H): 398.4. See also Bronner, S. M.; Bahnck K. B.; Garg, N. K.; Org. Lett., 11: 1007 (2009).

Provenance & Evidence