7-(Trimethylsilyl)hept-6-ynoic acid

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of hept-6-ynoic acid (1.90 g, 14.8 mmol) in anhydrous THF (90 mL) at −78° C. was treated with n-BuLi (2.3 M in hexanes, 14.5 mL, 33.3 mmol). After stirring for 2 min, TMSCl (5.8 mL, 46.0 mmol) was added. The reaction mixture was allowed to warm slowly to 25° C. and was stirred for 1 h. The reaction was quenched with the addition of aqueous 2 N HCl and extracted with CH2Cl2. The organic layer was dried over Na2SO4, filtered and concentrated. Column chromatography (SiO2, 4×6 cm, 20% EtOAc-hexanes) afforded 7-(trimethylsilyl)hept-6-ynoic acid (2.7 g, 13.6 mmol, 92%) as a white solid: 1NMR (CDCl3, 500 MHz) δ 2.40 (t, 2H, J=7.4 Hz), 2.24 (t, 2H, J=7.3 Hz), 1.78-1.72 (m, 2H), 1.62-1.56 (m, 2H), 0.15 (s, 9H). was stirred for 1 h The reaction was quenched with the addition of aqueous 2 N HCl extracted with CH2Cl2 The organic layer was dried over Na2SO4 filtered concentrated