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

HRID 2268826Notes

Reaction equation

HRID 2268826 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][CH2:11][C:12]([CH3:15])([CH3:14])[N:13]=2)=[CH:5][CH:4]=1.C([Li])CCC.CN([CH:24]=[O:25])C>C(OCC)C>[CH3:14][C:12]1([CH3:15])[CH2:11][O:10][C:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][C:7]=2[CH:24]=[O:25])=[N:13]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 3593374,5-Dihydro-2-(4-methoxyphenyl)-4,4-dimethyloxazoleHCID 178418339Butyllithium

Product 1

HCID 122201362-(4,4-Dimethyl-4,5-dihydro-oxazol-2-yl)-5-methoxy-benzaldehydeYield 84%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

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%). 1H-NMR (CDCl3) δ: 10.75(s,1H); 7.84-7.05(m,3H); 4.10(s,2H); 3.86(s,3H); 1.37(s,6H).

Workup

  1. customthe temperature below 5° C
  2. stirringAfter stirring overnight at room temperature
  3. temperaturethe mixture was cooled
  4. extractionextracted with water/ice
  5. extractionThe aqueous phase was extracted again with ethyl ether
  6. washThe organic phase was washed with water/NaCl
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-147312ba66d74ec7b3abfe9c7582638f
Source dataset
uspto-grants-2001_12
Patent number
US06329370B1

Reaction notes

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