HCID 67112061, compound → 3,6-Dihydro-2H-pyran-4-boronic acid pinacol ester

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Reaction Steps

Add Grubbs Catalyst, 2nd Generation (benzylidene-[1,3-bis(2,4,6-trimethylphenyl)imidazolidin-2-ylidene]-dichloro(tricyclohexylphosphine)ruthenium, 2.58 g, 0.03 eq) to a solution of 2-(3-allyloxy-1-methylene-propyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (23.4 g, 98.26 mmol) in dichloromethane (280 mL) and stir for 16 hours. Concentrate in vacuo and add hexanes (120 mL) to the residue. Stir for one hour and filter. Concentrate the filtrate in vacuo to give 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane as a tan solid (20.4 g, 99%). 1H NMR (300 MHz, CDCl3) δ 6.50 (m, 1H), 4.17 (q, J=2.7 Hz, 2H), 3.73 (t, J=5.4 Hz, 2H), 2.20 (m, 2H), 1.24 (s, 12H).

Provenance & Evidence