Nitrogen → 1-[2-(4,4-Dimethyl-4,5-dihydro-oxazol-2-yl)-5-methoxy-phenyl]-propan-1-one

HRID 2297402Notes

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:27])[CH2:25][CH3:26]>C(OCC)C.CCCCCC.[Cl-].[Cl-].[Zn+2].C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=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](=[O:27])[CH2:25][CH3:26])=[N:13]1

Participants

Conditions

Temperature: 0 °C

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 N2 at 0° C., was added with 2.5M n-butyl lithium (9.6 ml, 24.1 mmoles) in hexane. 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, at 0° C., dropwise added with the solution of the lithium derivative. At the end of the addition, the mixture was left at room temperature for 1.5 hours, then cooled to 0° C. and sequentially added with palladium acetate (0.25 g, 1.09 mmoles), triphenylphosphine (0.57 g, 2.19 mmoles) and, after 5 minutes, with propanoyl chloride (2.13 g, 23.02 mmoles). The mixture was left to stand for 20 hours, then poured into water/ice and extracted with ethyl acetate. The organic phase was anhydrified, discoloured and brought to dryness to give 6.6 g of the title compound (yield: 75%)

Workup

customwent on for 4 hours
customwas prepared and, at 0° C.
additionAt the end of the addition
waitThe mixture was left
waitto stand for 20 hours
extractionextracted with ethyl acetate

Sources & evidence

ORD record: ord-f17daa52062b4b7faa1703dd078abc05
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06492360B1

Reaction notes

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