Hydrochloric Acid → Ethyl 2-(1,6-dihydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acrylate

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Reaction Steps

Into a 50-mL round-bottom flask was placed a solution of 2-methyl-4-(tetrahydro-2H-pyran-2-yloxy)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde (5 g, 14.45 mmol, 1.00 equiv) in ethyl acrylate (10 mL), then added DABCO (2.42 g, 21.61 mmol, 1.50 equiv). The resulting solution was stirred for 24 h at room temperature. The pH value of the solution was adjusted to 3 with HCl (3N) and stirred for 2 h at 30° C. The resulting solution was extracted with 3×50 mL of ethyl acetate. The organic layers were combined, washed with 2×20 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (1:1). This resulted in 3.0 g (75%) of ethyl 2-(1,6-dihydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acrylate as a white solid.

Provenance & Evidence