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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2297398Generated: October 30, 2026

Dimethylformamide → 2-(4,4-Dimethyl-4,5-dihydro-oxazol-2-yl)-5-methoxy-benzaldehyde

https://huagongshe.com/reaction/2297398

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
Reactant4,5-Dihydro-2-(4-methoxyphenyl)-4,4-dimethyloxazoleHCID 359337—
ReactantButyllithiumHCID 178418339—
SolventDiethyl EtherHCID 3283—
Product2-(4,4-Dimethyl-4,5-dihydro-oxazol-2-yl)-5-methoxy-benzaldehydeHCID 1222013684%

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

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06492360B1
Source datasetuspto-grants-2002_12
ORD IDord-966ff28bd39a431f8ff7211cee27174b
Source noteuspto-grants-2002_12