Trimethylsilyl iodide → HCID 76684173, compound

Participants

Reaction Conditions

Reaction Steps

Into a 20 ml vial, the product from step (b) (103 mg, 0.394 mmol) in CHCl3 (2 ml) was placed. To this solution, TMSI (468 μL, 3.44 mmol) was added. The reaction mixture was heated at 60° C. for 2 hours and then at room temperature for 16 hours. The volatiles were evaporated in vacuo and 2M HCl (5 ml) and water (25 ml) were added. The aqueous mixture was washed with diethyl ether (2×). The aqueous layer was then basified with 2M NaOH to pH 10 and 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 as a yellow oil (53 mg). 1H NMR (300 MHz, CDCl3) δ 6.99-6.91 (m, 2H); 3.09-2.92 (m, 8H); 2.79-2.71 (m, 2H); 2.24-2.14 (m, 1H); 2.05-1.98 (m, 1H); 1.30-1.21 (m, 2H); 0.88-0.78 (m, 1H); 0.51-0.44 (m, 2H); 0.31-0.026 (m, 1H); 0.23-0.17 (m, 1H); MS: ESI (positive): 228, (M+1).

Provenance & Evidence