(Z)-4,4,5,5-Tetramethyl-2-(1-phenylbut-1-en-1-yl)-1,3,2-dioxaborolane synthesis
- Product Name:(Z)-4,4,5,5-Tetramethyl-2-(1-phenylbut-1-en-1-yl)-1,3,2-dioxaborolane
- CAS Number:1283231-74-2
- Molecular formula:C16H23BO2
- Molecular Weight:258.16
Yield:1283231-74-2 80%
Reaction Conditions:
Stage #1: propiophenonewith magnesium methanolate;lithium diisopropyl amide in 1,2-dimethoxyethane at -30; for 0.0833333 h;Inert atmosphere;Sealed tube;
Stage #2: bis(pinacol)diborane in 1,2-dimethoxyethane at 130; for 12 h;Inert atmosphere;
Steps:
1
Under a nitrogen atmosphere, add phenylbutanone (0.5mmol, 1.0equiv., 74.0mg), magnesium methoxide (1.0equiv., 43.2mg), ethylene glycol dimethyl ether (1.5mL) and magnets to the baked in the 25mL glass pressure tube. Subsequently, the glass pressure tube was cooled to -30°C, lithium diisopropylamide (1.1 equiv.) was added, and the mixture was stirred for 5 minutes. After the stirring was completed, the diboronic acid pinacol borate (1.2 equiv., 152.4 mg) was added at room temperature and the temperature was raised to 130° C. and stirred for 12 hours. After the reaction, ethyl acetate was added to the system for extraction, and the product was separated by column chromatography with a yield of 80% and Z:E>20:1.
References:
CN112010881,2020,A Location in patent:Paragraph 0049-0052
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