Chlorotrimethylsilane → HCID 58292727, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of zinc dust (1.26 g, 19.30 mmol) in THF (8 mL) was treated with chlorotrimethylsilane (0.30 mL, 2.40 mmol) at 40° C. The mixture was heated at 55° C. for 15 minutes, the cooled to 37° C. Ethyl bromoacetate (1.68 mL, 17.70 mmol) was added dropwise (refluxed gently upon addition), then stirred for 5 min. The suspension was allowed to settle at room temperature. The Reformasky reagent (approximately 1.7 M stock solution, 1.5 mL, 2.55 mmol) was transferred via syringe to a dry flask, then cooled to 0° C. 2-Methyl-4-phenoxy-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzaldehyde (0.50 g, 1.48 mmol) in THF (5 mL) was added dropwise to the reagent, then stirred at 0° C. for 4 h. The mixture was quenched with saturated NH4Cl, extracted with EtOAc, dried (Na2SO4), filtered and concentrated to a yellow oil. The oil was purified by column chromatography (SiO2, EtOAc/hexanes; 1:5 to 1:1 gradient) to afford (1-hydroxy-4-methyl-6-phenoxy-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester (0.22 g, 46%), as a yellow oil. 1H NMR (400 MHz, DMSO-d6) δ 9.18 (s, 1H), 7.40 (t, J=7.42 Hz, 2H), 7.16 (t, J=7.42 Hz, 1H), 7.07 (d, J=2.35 Hz, 1H), 7.02-6.97 (m, 3H), 5.51 (dd, J=9.33, 2.34 Hz, 1H), 4.05 (q, J=7.03 Hz, 2H), 3.14 (dd, J=15.63, 2.74 Hz, 1H), 2.89 (s, 3H), 2.33-2.26 (m, 1H), 1.14 (t, J=7.03 Hz, 3H); MS (ES) m/z: 325 (M−1).

Provenance & Evidence