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3-trimethylsilanylpropynoic acid (3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl) amide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
15%
3- (Trimethylsilyl) propynoic acid (l. Og, 7 mmol) was dissolved in DCM (lOml) under nitrogen and cooled to 0C. Oxalyl chloride (0. 6ml, 7 mmol) was added dropwise, keeping the temperature below 5C. The solution became orange. At the end of the addition, the mixture was maintained at room temperature for one hour, then aminothiophene EO (1.25g, 7 mmol) was added as a solution in THF (10ml). The reaction mixture was stirred for 4 hours at room temperature and then treated with saturated aqueous ammonium chloride and extracted with DCM. The combined organic extracts were dried over magnesium sulphate and evaporated under reduced pressure. Purification of the residue by flash chromatography gave the desired product (0.25g, 15%) as an amorphous solid. 'H NMR 8H (300MHz, CDC13) : 8.55 (1H, br s), 2.6 (4H, m), 1.85 (4H, m) and 0.3 (9H, s) ppm; ni/z (-ve ion): 301 (M-H).
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