(E)-But-1-en-1-ylboronic acid synthesis
- Product Name:(E)-But-1-en-1-ylboronic acid
- CAS Number:1005452-36-7
- Molecular formula:C4H9BO2
- Molecular Weight:99.92
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Yield:1005452-36-7 53%
Reaction Conditions:
Stage #1: but-1-ynewith (+)-α-pinene;dimethyl sulfide borane in tetrahydrofuran at 0 - 20;
Stage #2: with acetaldehyde in tetrahydrofuran at 40;
Stage #3: with water in tetrahydrofuran at 20;
Steps:
4.1.2 General procedure of hydroboration and hydrolysis (GP-B)
A bomb flask was charged with THF and BH3·SMe2 at 0 °C, then (+)-α-pinene was added dropwise. The solution was stirred at 0 °C for 10 min then allowed to warm to rt and stirred at rt for 2-3 h, during which time a white precipitate formed. The solution was recooled to 0 °C and alkyne was added to it, resulting in a clear, colorless solution. The flask was then sealed with a Teflon screw cap and the mixture was stirred at 0 °C for 5-30 min, warmed to rt, and stirred at rt for 1.5-2.5 h. The solution was recooled to 0 °C and acetaldehyde was added. The bomb flask was resealed with the Teflon screw cap and the reaction mixture was stirred at 40 °C for 4.5-5 h. It was allowed to cool to 0 °C and H2O was added. Stirring was continued for 3-7 h at rt, and then the solution was diluted with EtOAc. Purification was performed by partition under basic conditions or by silica gel chromatography to afford the target molecule.
References:
Mita, Yusuke;Dodo, Kosuke;Noguchi-Yachide, Tomomi;Hashimoto, Yuichi;Ishikawa, Minoru [Bioorganic and Medicinal Chemistry,2013,vol. 21,# 4,p. 993 - 1005]
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13292-87-0
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$22.89/5ml
1005452-36-7
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