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CAS No. : | 1444-65-1 | MDL No. : | MFCD00001629 |
Formula : | C12H14O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DRLVMOAWNVOSPE-UHFFFAOYSA-N |
M.W : | 174.24 | Pubchem ID : | 95592 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | 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 |
---|---|---|
With diphenyl hydrogen phosphate; silver carbonate; In hexane; at 40℃; for 23.0h; | General procedure: A dry single-necked flask was charged with 2-alkynylaldehyde 1 (0.4 mmol, 1 equiv), ketone 2 (0.8 mmol, 2 equiv), and diphenylphosphate (10 mg, 0.04 mmol, 10 mol %) in hexane (2.4 mL), and silver carbonate (2.75 mg 0.01 mmol, 2.5 mol%) was added. The mixture was heated to 40 C and stirred until the 2-alkynylaldehyde was completely consumed (progress of the reaction was monitored by TLC). The hexane was evaporated and the mixture was diluted in EtOAc (50 mL) and washed three times with water. The organic layer was dried over anhydrous Na2SO4 and filtered. After evaporating the EtOAc, the crude product was dissolved in dichloromethane and purified by column chromatography (silica gel; pentane/EtOAc, 96:4) to give pure 1H-isochromenes 3 as yellow oils or as colorless solids. In the case of phenylacetone and 2-phenylcyclohexanone as ketone nucleophiles, the crude product was directly purified by flash chromatography on silica gel. |
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