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CAS No. : | 141567-53-5 | MDL No. : | MFCD08703638 |
Formula : | C5H7NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | BGPDSEDYUPFTBI-UHFFFAOYSA-N |
M.W : | 113.11 | Pubchem ID : | 5324810 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H319 | 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 |
---|---|---|
96% | With diisobutylaluminium hydride; sodium fluoride In tetrahydrofuran; methanol; water; toluene | A solution of ethyl 2-methyloxazole-4-carboxylate (0.31 g, 2.0 mmol) in tetrahydrofuran (5 mL) was chilled to -65° C. and diisobutylaluminum hydride (4.1 mL of a 1 N solution in toluene, 4.1 mmol) was added dropwise over 15 min. The solution was allowed to warm to ambient temperature and stir 15 min. The reaction was chilled to 5° C. and carefully quenched by addition of methanol (2 mL). The reaction mixture was returned to ambient temperature and water (0.18 mL) was added followed by sodium fluoride 1.68 g). This mixture was stirred 30 min, then dried with magnesium sulfate and filtered. The filtrate was concentrated and azeotroped with chloroform to afford 0.215 g (96percent) of 4-hydroxymethyl-2-methyloxazole as a pale oil which had: NMR δ 7.45 (s, 1H), 4.52 (d, J=6 Hz, 2H), 3.41 (br s, 1H), 2.42 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With sodium fluoride In tetrahydrofuran; methanol; water; toluene | A solution of ethyl 2-methyloxazole-4-carboxylate (0.31 g, 2.0 mmol) in tetrahydrofuran (5 mL) was chilled to -65° C. and disobutylaluminum hydride (4.1 mL of a 1 N solution in toluene, 4.1 mmol) was added dropwise over 15 min. The solution was allowed to warm to ambient temperature and stir 15 min. The reaction was chilled to 5° C. and carefully quenched by addition of methanol (2 mL). The reaction mixture was returned to ambient temperature and water (0.18 mL) was added followed by sodium fluoride 1.68 g). This mixture was stirred 30 min, then dried with magnesium sulfate and filtered. The filtrate was concentrated and azeotroped with chloroform to afford 0.215 g (96percent) of 4-hydroxymethyl-2-methyloxazole as a pale oil which had: NMR δ 7.45 (s, 1 H), 4.52 (d, J=6 Hz, 2 H), 3.41 (br s, 1 H), 2.42 (s, 3 H). |