Acrolein → t-butyl {2-chloro-5-[(1E)-3-oxo-1-propenyl]phenoxy}acetate

HRID 1352857Notes

Reaction equation

[Cl:1][C:2]1[CH:16]=[CH:15][C:14](I)=[CH:13][C:3]=1[O:4][CH2:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].[CH:18]([CH:20]=[CH2:21])=[O:19].C(=O)([O-])[O-].[Na+].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>CN(C)C=O.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:1][C:2]1[CH:16]=[CH:15][C:14](/[CH:21]=[CH:20]/[CH:18]=[O:19])=[CH:13][C:3]=1[O:4][CH2:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7]

Participants

Conditions

Temperature: 60 °C

Procedure

t-Butyl (2-chloro-5-iodophenoxy)acetate (851 mg, 2.00 mmol) was dissolved in dimethylformamide under an atmosphere of nitrogen, and thereto were acrolein (0.400 ml, 6.00 mmol), sodium carbonate (0.510 g, 6.00 mmol), benzyltriethylammonium chloride (683 mg, 3.00 mmol) and palladium acetate (14.0 mg, 60.0 μmol). The mixture was stirred for 3 hours at 60° C. The reaction mixture was cooled and thereto was added sodium thiosulfate. The mixture was extracted with ethyl acetate and the organic layer was washed with sodium thiosulfate, 10% aqueous citric acid solution, water, an aqueous saturated sodium hydrogencarbonate solution and an aqueous saturated sodium chloride solution in the order, and dried over magnesium sulfate. The solvent was removed to give the subject compound as yellow crystals (631 mg, quantitatively).

Workup

temperatureThe reaction mixture was cooled
extractionThe mixture was extracted with ethyl acetate
washthe organic layer was washed with sodium thiosulfate, 10% aqueous citric acid solution, water
dry with materialan aqueous saturated sodium hydrogencarbonate solution and an aqueous saturated sodium chloride solution in the order, and dried over magnesium sulfate
customThe solvent was removed

Sources & evidence

ORD record: ord-7c6f8d7f48784c63b430ebf495aba01e
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07220773B2

Reaction notes

Loading…