Trimethylsilyl iodide → HCID 76684635, compound

Participants

Reaction Conditions

Reaction Steps

Into a glass vial, the product from step (c) dissolved in CHCl3 (3 ml) was placed. To this solution, TMSI (0.31 ml, 2.3 mmol) was added. The reaction mixture was heated to 60° C. for 4 h and then allowed to cool to room temperature. The reaction mixture was quenched by addition of 2N HCl (5 ml) and further diluted with water (25 ml). The aqueous mixture was washed with diethyl ether (2×). The aqueous layer was basified by addition of 5N KOH to pH 10. The basic solution was extracted with DCM (3×). The combined DCM extracts were washed with brine, dried over Na2SO4, and solvent evaporated in vacuo to give the title product. 1H NMR (CDCl3) δ 6.95 (d, J=7.5 Hz, 1H), 6.90 (d, J=7.5 Hz, 1H), 3.36-3.27 (m, 1H), 3.08-2.90 (m, 7H), 2.82-2.74 (m, 1H), 2.27-2.16 (m, 1H), 1.89 (bs, 1H), 1.80-1.73 (m, 1H), 1.33-1.22 (m, 2H), 1.12 (d, J=6.9 Hz, 3H); MS: ESI (positive): 202 (M+H).

Provenance & Evidence