Chlorotrimethylsilane → HCID 68292479, compound

Participants

Reaction Conditions

Reaction Steps

To a round bottom flask was added (Z)-ethyl 2-(4-methoxyphenylimino)acetate (4000 mg, 19.30 mmol) and DMF (30 mL). The reaction was cooled to 0° C. Then, 1-bromo-3-methylbut-2-ene (3740 mg, 25.09 mmol) was added to the reaction followed by zinc (1641 mg, 25.09 mmol) and a drop of TMS-Cl (0.247 mL, 1.93 mmol). The reaction mixture was slowly warmed up to rt over 45 min and then stirred at rt for 20 min. The reaction mixture was cooled to 0° C. and aqueous 5% NH4Cl (10 mL) was added to the reaction. The reaction was extracted with ether (3×50 mL). The combined ether layer was washed with water (100 mL) and saturated aqueous NaCl (100 mL). The organic layer was separated, dried over MgSO4, filtered and concentrated. The residue was purified using silica gel chromatography (ISCO system) eluting with a gradient of 0-60% EtOAc/Hex to give ethyl 2-(4-methoxyphenylamino)-3,3-dimethylpent-4-enoate (1.1 g, 4.0 mmol, 21% yield) as a yellow oil. 1H NMR (500 MHz, CDCl3) δ ppm 6.76 (d, J=9.35 Hz, 2H), 6.60 (d, J=8.80 Hz, 2H), 5.96 (dd, J=17.32, 10.72 Hz, 1H), 5.19-5.08 (m, 2H), 4.15 (q, 2H), 3.85 (s, 1H), 3.77-3.71 (m, 4H), 1.23 (t, J=7.15 Hz, 3H), 1.21 (s, 3H), 1.17 (s, 3H); 13C NMR (126 MHz, CDCl3) δ ppm 173.09, 152.71, 143.47, 141.42, 115.30, 114.79, 113.92, 66.02, 60.54, 55.69, 40.06, 24.89, 23.70, 14.27.

Provenance & Evidence