Trimethylsilyldiazomethane → HCID 68528114, compound

Participants

Reaction Conditions

Reaction Steps

An anhydrous solution of methanol:toluene (2:5) (10.5 mL) was used to solubilize 7-(3-methoxyphenyl)heptanoic acid (0.159 g, 0.673 mmol) under an atmosphere of argon and the solution was then cooled to 0° C. Stirring was initiated and a 2 M solution of TMSCHN2 (in hexanes) (0.740 mL, 1.48 mmol) was added dropwise to the reaction solution. The yellow solution was allowed to stir for 30 minutes at room temperature before again being cooled to 0° C. The reaction was quenched with the dropwise addition of acetic acid until the characteristic yellow color of diazomethane dissipated. The solvent was removed under vacuum and the resultant suspension taken in ethyl acetate. The organic phase was washed with saturated sodium bicarbonate then brine and dried over sodium sulfate. The solvent was removed under vacuum and the target product was purified as a light yellow oil (92%, 0.139 g) using flash column chromatography (silica) with a 10% ethyl acetate:hexanes mobile phase: 1H NMR (500 MHz, CDCl3) δ 7.19 (t, 1H), 6.74 (q, 3H), 3.80 (s, 3H), 3.67 (s, 3H), 2.59 (t, 2H), 2.31 (t, 2H), 1.63 (m, 4H), 1.36 (m, 4H); 13C NMR (500 MHz, CDCl3) δ 174.17, 159.60, 144.31, 129.17, 120.82, 114.17, 110.86, 55.06, 51.41, 35.93, 34.05, 31.17, 29.01, 28.91, 24.89.

Provenance & Evidence