Hydrochloric Acid → HCID 58292542, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of zinc dust (5.35 g, 82.3 mmol) in THF (10 mL) was added trimethylsilyl chloride (1.1 g, 10.15 mmol) at 40° C. The mixture was heated to 55° C. and stirred for 45 minutes. After cooling down to 37° C., ethyl bromoacetate (7.58 mL, 74.87 mmol) was slowly added to the reaction mixture at 37-40° C. After addition, the resulting mixture was allowed to cool to room temperature over 30 minutes. This solution was added to a solution of 2-ethyl-4-(tetrahydro-pyran-2-yloxy)-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzaldehyde (2.07 g, 5.39 mmol) in THF (6 mL) at 0° C. The mixture was stirred for 10 minutes before treating with 3 N HCl and extracted with EtOAc (2×25 mL). The organic extracts were washed with brine, dried over anhydrous MgSO4 and concentrated in vacuo. The residue was purified by silica gel flash column chromatography and lyophilized to give (4-ethyl-1,6-dihydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester(0.380 g, 27%). 1H NMR (400 MHz, DMSO-d6δ 9.30 (s, 1H), 9.02 (s, 1H), 6.88 (s, 1H), 6.68 (s, 1H), 5.40 (m, 1H), 4.00 (m, 2H), 3.00 (m, 1H), 2.50 (m, 2H), 2.20 (m, 1H), 1.20 (m, 3H).

Provenance & Evidence