Chlorotrimethylsilane → HCID 10539357, compound

Participants

Reaction Steps

To a solution of 3 g (16.4 mmol) of 3-thiophenecarboxylic acid, N,N-diethylamide, from step 2a above, in 20 mL of THF cooled to -78° C. and stirred under N2 was added 1.68 g (2.1 mL, 16.4 mmol) of N,N,N',N'-tetramethylenediamine (TMEDA), followed by 12.6 mL of a 1.3M solution of 2-butyl lithium in cyclohexane (16.4 mmol), and the reaction was stirred for 1 hour. Chlorotrimethylsilane (1.78 g, 2.1 mL, 16.4 mmol) was added, and the solution was stirred for 45 min, then poured into 100 mL of water. The mixture was extracted 3× with methylene chloride, and the solvent was washed with brine, dried over MgSO4, concentrated, and purified by flash chromatography, eluting with 3:1 hexane:ethyl acetate to afford 1.4 g (38% yield) of the title product as an oil. MS 256 (M+H)+. NMR (CDCl3) δ:7.51 (d, 1 H, J=5 Hz), 7.10 (d, 1 H, J=5 Hz), 3.60-3.50 (bm, 2H), 3.3-3.10 (bm, 2H), 1.30-1.20 (bm, 3H), 1.15-1.05 (bm, 3H), 0.34 (s, 9H).

Provenance & Evidence