Identification | More | [Name]
3-Furanboronic acid pinacol ester | [CAS]
248924-59-6 | [Synonyms]
3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)FURAN 3-FURANBORONIC ACID, PINACOL ESTER FURAN-3-BORONIC ACID PINACOL ESTER 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)furane 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)furan,min.97% 3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)FURAN, MIN. 97% | [Molecular Formula]
C10H17BO4 | [MDL Number]
MFCD03453669 | [Molecular Weight]
212.05 | [MOL File]
248924-59-6.mol |
Hazard Information | Back Directory | [Synthesis]
GENERAL METHOD: 3-bromofuran (1 mmol), pinacol ester of bisboronic acid (1.2 mmol) and dioxane (5 mL) were added to a 25 mL round bottom flask. KOAc (2 mmol) was then added and the mixture was stirred for 5 min at room temperature. PdII-TpTP catalyst (0.15 mol%) was added and the reaction mixture was placed in an oil bath preheated to 110 °C and refluxed with continuous stirring in the open system. The reaction progress was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the mixture was cooled to room temperature, diluted with water (20 mL) and extracted with tert-butyl methyl ether (3 x 10 mL). The organic layers were combined and concentrated to give the crude product. The crude product was purified by silica gel column chromatography using a mixture of ethyl acetate and hexane (1:30) as eluent. | [References]
[1] Organic Letters, 2014, vol. 16, # 17, p. 4562 - 4565 [2] Journal of the American Chemical Society, 2017, vol. 139, # 2, p. 607 - 610 [3] Synlett, 2018, vol. 29, # 8, p. 1055 - 1060 |
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