Hydrochloric Acid → 2-(5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiazol-2-yl)propan-2-ol

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Reaction Conditions

Reaction Steps

To a solution of 2-(1,3-thiazol-2-yl)propan-2-ol (40 g, 0.28 mol) in THF (400 mL) was add n-butyllithium (2.5 M in hexanes, 260 mL, 0.64 mol) dropwise at −78° C. After 30 minutes, 4,4,5,5-tetramethyl-2-(propan-2-yloxy)-1,3,2-dioxaborolane (65 g, 0.35 mol) was added at −78° C. The reaction solution was then stirred at −78° C. After 1 hour, the reaction mixture was quenched with acetic acid, filtered, and concentrated under reduced pressure. The residue was diluted with hydrochloric acid (3.0 M solution in diethyl ether, 110 mL, 0.33 mol) and the mixture was filtered to afford 2-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-thiazol-2-yl]propan-2-ol. MS ESI calc'd. for C12H21BNO3S [M+H]+ 270. found 270. 1H NMR (300 MHz, DMSO-d6): δ 8.01 (s, 1H), 1.49 (s, 6H), 1.28 (s, 12H).

Provenance & Evidence