Trifluoroacetic acid → HCID 86718317, compound

Participants

Reaction Conditions

Reaction Steps

Triethylsilane (178 μL, 1.11 mmol) was added slowly to 2 mL of trifluoroacetic acid (TFA) at room temperature. The mixture was cooled to 0° C. and mixed for 30 min. A fresh solution of (2-methylazulen-1-yl)(4-methylthiazol-2-yl)methanol 5 (100 mg, 0.371 mmol) in dichloromethane was then added slowly to the mixture being stirred at 0° C. The reaction was kept at 0° C. for 2 h and then warmed to room temperature. Afterward, the mixture was poured into cold 20% KOH to quench the reaction. The organic layer was extracted into diethyl ether and washed with water and brine, dried with MgSO4 and purified using flash chromatography (ethyl acetate and hexane). The purified material was dried down into a blue solid. Yield: 64.3 mg, 68%. 1H NMR (400 MHz, CDCl3) δ 8.19 (t, J=10.38 Hz, 2H), 7.49 (t, J=9.90 Hz, 1H), 7.21 (s, 1H), 7.17-7.10 (m, 2H), 6.60 (s, 1H), 4.68 (s, 2H), 2.60 (s, 3H), 2.42 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 171.8, 152.1, 149.0, 140.1, 137.0, 135.8, 134.4, 131.5, 123.2, 122.7, 117.8, 113.1, 29.3, 17.0, 15.0. HRMS (ES) calcd. MH+ [C16H16NS]+ 254.0925. found 254.0990.

Provenance & Evidence