HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → 2-(4,4-Dimethyl-4,5-dihydro-oxazol-2-yl)-5-methoxy-benzaldehyde
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | 4,5-Dihydro-2-(4-methoxyphenyl)-4,4-dimethyloxazole | HCID 359337 | — |
| Reactant | Butyllithium | HCID 178418339 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Product | 2-(4,4-Dimethyl-4,5-dihydro-oxazol-2-yl)-5-methoxy-benzaldehyde | HCID 12220136 | 84% |
Reaction Steps
In dry environment under N2, 2-(4-methoxy-phenyl)-4,4-dimethyl-4,5-dihydro-oxazole (20 g, 0.097 mole), prepared as described in example 1, was dissolved in ethyl ether (200 ml) and added at −2° C. with n-butyl lithium (44 ml, 0.11 mole), keeping the temperature below 5° C. The mixture was stirred and after 4 hours added with DMF (15.4 g, 16.3 ml, 0.21 mole). After stirring overnight at room temperature, the mixture was cooled and extracted with water/ice. The aqueous phase was extracted again with ethyl ether. The organic phase was washed with water/NaCl, discoloured with charcoal, anhydrified and concentrated under vacuum to give 19 g of the title compound (yield: 84%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06492360B1 |
| Source dataset | uspto-grants-2002_12 |
| ORD ID | ord-966ff28bd39a431f8ff7211cee27174b |
| Source note | uspto-grants-2002_12 |