Trimethylsilyl iodide → HCID 76684633, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of the product from step (c) (20 mg, 0.07 mmol) in chloroform (2 ml) was added TMSI (0.092 ml, 0.7 mmol). The reaction mixture was heated to 60° C. for 6 hours after which LCMS indicated no starting material. The reaction mixture was cooled to RT and the volatiles were removed in vacuo. The residue was dissolved in 1N HCl (10 ml) and washed with diethyl ether (3×). The aqueous layer pH was then adjusted to 12 by addition of 2M NaOH. The aqueous mixture was then extracted with DCM (3×). The combined DCM extracts were washed with brine, dried (Na2SO4), and solvent evaporated in vacuo to give the titled compound as a colorless oil (9 mg). 1H NMR (300 MHz, CDCl3) δ 6.99 (d, J=7.8 Hz, 1H); 6.96 (d, 7.8 Hz, 1H); 3.47-3.34 (m, 4H); 2.98-2.82 (m, 8H); 2.09 (bs, 1H); MS: ESI (positive): 224 (M+1).

Provenance & Evidence