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ChemicalBook CAS DataBase List 3,6-dihydropyran-5-boronic ester

3,6-dihydropyran-5-boronic ester synthesis

3synthesis methods
-

Yield:212127-81-6 60%

Reaction Conditions:

with dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2;potassium acetate in 1,4-dioxane at 80;Inert atmosphere;

Steps:

2.2 Step 2 2-(5,6-dihydro-2H-pyran-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborane
Add 5,6-dihydro-2H-pyran-3-yltrifluoromethanesulfonate 2b (600 mg, 2.59 mmol), Pinacol diborate (788 mg, 3.10 mmol), Potassium acetate (760 mg, 7.76 mmol), [1,1'-Bis(diphenylphosphine)ferrocene] palladium dichloride dichloromethane complex(63 mg, 0.0776 mmol) and 1,4-dioxane (25 mL),The argon was replaced 3 times, and the reaction was carried out in an 80 ° C oil bath overnight.After the reaction, the reaction solution was cooled and poured into water (20 mL). It was then extracted with ethyl acetate (50 mL x 3). The organic phases were combined and washed with saturated brine (50 mL x 3), then dried over anhydrous sodium sulfate,Filtration and concentration, the residue was purified by column chromatography (petroleum ether / ethyl acetate = 10/1) to give 2- (5,6-dihydro-2H-pyran-3-yl) -4,4,5,5-Tetramethyl-1,3,2-dioxaborane 2c (1.2 g, colorless oil), yield: 60%.

References:

Shanghai Meidixi Bio-pharmaceutical Co., Ltd.;Meidixipuya Pharmaceutical (Shanghai) Co., Ltd.;Ren Feng;Wang Xianlian;Xu Yongmei;Chen Chunlin;Cai Jinna CN110194773, 2019, A Location in patent:Paragraph 0071; 0072

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