Nitrogen → [2-(4,4-Dimethyl-4,5-dihydro-oxazol-2-yl)-5-methoxy-phenyl]-phenyl-methanone

HRID 2297406Notes

Reaction equation

HRID 2297406 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.N#N.C([Li])CCC.[Li].[C:24](Cl)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(OCC)C.CCCCCC.[Cl-].[Cl-].[Zn+2].Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[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[C:24]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:31])=[N:13]1

Participants

10

Reactant 5

HCID 947NitrogenHCID 7412Benzoyl chlorideHCID 3593374,5-Dihydro-2-(4-methoxyphenyl)-4,4-dimethyloxazoleHCID 3028194LithiumHCID 178418339Butyllithium

Product 1

HCID 18381663[2-(4,4-Dimethyl-4,5-dihydro-oxazol-2-yl)-5-methoxy-phenyl]-phenyl-methanoneYield 52%

Reagents, catalysts & solvents 4

HCID 3007855ZincchlorideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent

Procedure

A solution of 2-(4-methoxy-phenyl)-4,4-dimethyl-4,5-dihydro-oxazole (4.5 g, 21.9 mmoles), prepared as described in example 1, in dry ethyl ether (90 ml), under stirring and dry N2 at 0° C., was added with 2.5M n-butyl lithium (9.6 ml, 24.1 mmoles) in hexane, and the reaction went on for 4 hours. In another flask a suspension of ZnCl2 (4.48 g, 33 mmoles) in dry ethyl ether (60 ml) was prepared and dropwise added with the solution of the lithium derivative at 0° C. and, after 1 hour, with benzoyl chloride (3.24 g, 23.02 mmoles). The mixture was left at room temperature for 3 hours, then added with bis(triphenylphosphine)palladium chloride (280 mg) and, after 3 days, poured into water/ice and extracted with ethyl acetate. The organic phases were washed with water, anhydrified and brought to dryness to give 3.5 g of the title compound (yield: 52%).

Workup

  1. customwent on for 4 hours
  2. customwas prepared
  3. extractionextracted with ethyl acetate
  4. washThe organic phases were washed with water

Sources & evidence

ORD record
ord-40b13ea62eca445793b64bd17084fe0a
Source dataset
uspto-grants-2002_12
Patent number
US06492360B1

Reaction notes

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