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CAS No. : | 23462-75-1 | MDL No. : | MFCD00182426 |
Formula : | C5H8O2 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | URUUZIAJVSGYRC-UHFFFAOYSA-N |
M.W : | 100.12 | Pubchem ID : | 90109 |
Synonyms : |
|
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
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 n-butyllithium; citric acid; In tetrahydrofuran; hexane; benzene; | Reference Example 22 In benzene (100 ml) was dissolved tetrahydropyran-3-one (35.1 g) followed by addition of cyclohexylamine (40 ml) with ice-cooling the mixture was-stirred at the same temperature for 30 minutes and, then, refluxed for 1 hour, with the byproduct water being distilled off. After cooling to room temperature, the reaction mixture was added dropwise to 1.6M n-butyllithium in hexane (230 ml) in dry THF (350 ml) with ice-cooling over 30 minutes and the mixture was stirred at the same temperature for 30 minutes. Then, a solution of 2-(tert-butyldimethylsilyloxy)ethyl iodide (75 g) in THF (140 ml) was added with ice-cooling over 20 minutes and the mixture was stirred at the same temperature for 1 hour. Then, 10percent aqueous solution of citric acid (1 l) was added and the mixture was vigorously stirred. This reaction mixture was shaken with hexane (3 l) and the organic layer was separated. The organic layer was washed with water and aqueous sodium chloride solution in that order, and dried over anhydrous magnesium sulfate. The solvent was then distilled off under reduced pressure and the residue was purified by column chromatography (stationary phase: silica gel 1 kg; ethyl acetate-hexane 1:10) to give 42.8 g of 4-[2-(tert-butyldimethylsilyloxy)ethyl]-3-oxotetrahydropyran as light yellow oil. IR (Neat): 2960, 2930, 2850, 1720 cm -1 |
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