CAS No. : | 273731-82-1 | MDL No. : | MFCD16295105 |
Formula : | C11H15BO4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VSQZZPPWTRWPTM-UHFFFAOYSA-N |
M.W : | 222.05 | Pubchem ID : | 53217094 |
Synonyms : |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example I5-(4,4, 5, 5-Tetramethyl- 1, 3,2-dioxaborolan-2-yl)furan-2-carbaldehyde (VIla)A 2.5M solution of butyllithium in hexanes (50 ml, 0.125 mol) was added to a solution of <strong>[13529-27-6]diethylacetal furan-2-carbaldehyde</strong> (17.0 g, 0.1 mol) in dimethoxyethane (100 mL) with a linear dispenser at the temperature of -50C during 1 hour and the mixture wasstirred under nitrogen at this temperature for 4 hours. Then, 2-isopropoxy-4,4,5,5- tetramethyl-l,3,2-dioxaborolane (24.0 g, 0.129 mol) was added with a linear dispenser during 30 minutes and the mixture was stirred at -40C for 2 hours and then stirred without cooling under nitrogen for 4 hours (the internal temperature rose to 20C). 2.5M HCI (100 ml) was added dropwise to the dark reaction mixture and themixture was stirred at the room temperature for 30 minutes. After addition of ethyl acetate (200 ml), the organic layer was separated and the aqueous layer was shaken with ethyl acetate (2 x 25 ml). The combined organic fractions were washed with water (4 x 25 ml) and dried with MgSO4. 18.3 g of the crude product was obtained containing, according to HPLC, 96.8% of the desired compound in the form of ayellowish liquid. The product contained 2-3% of the corresponding boronic acid. If it is undesired, it can be easily removed by addition of a small amount of pinacol to a solution of the crude compound VIla in a suitable solvent.1H NMR (250 MHz, DMSOd6): 1.30(s, 12 H), 7.23(d, J= 3.6 Hz, IH), 7.51 (d, J3.6 Hz, I H), 9.71 ppm (s, 1 H). |
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