Dimethyl Sulfate → 4-methoxy-3-[3-[3-(2-cyanoethenyl)phenyl]-1-oxo-2-propenyl]-6-methyl-2H-pyran-2-one

HRID 639737Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[O:5][C:4](=[O:9])[C:3]=1[C:10](=[O:23])[CH:11]=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH:19]=[CH:20][C:21]#[N:22])[CH:14]=1.[H-].[Na+].S(OC)(O[CH3:30])(=O)=O>CN(C)P(N(C)C)(N(C)C)=O>[CH3:30][O:1][C:2]1[CH:7]=[C:6]([CH3:8])[O:5][C:4](=[O:9])[C:3]=1[C:10](=[O:23])[CH:11]=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH:19]=[CH:20][C:21]#[N:22])[CH:14]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a mixture of 20 ml of hexamethylphosphoramide and 3.50 g of 4-hydroxy-3-[3-[3-(2-cyanoethenyl)phenyl]-1-oxo-2-propenyl]-6-methyl-2H-pyran-2-one was added 0.46 g of sodium hydride (60% oily) at about 0° C., and a temperature was raised to 50° C., followed by stirring for 1 hour and 10 minutes. Then, 3.22 g of dimethyl sulfate was added thereto, and the mixture was stirred at 50° C. for 4 hours. Thereafter, the reaction mixture was added to ice water, and the mixture was extracted with ethyl acetate. The organic layer washed with an aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 1.12 g of 4-methoxy-3-[3-[3-(2-cyanoethenyl)phenyl]-1-oxo-2-propenyl]-6-methyl-2H-pyran-2-one [Compound No. (2a)] as a pale yellow crystal.

Workup

stirringthe mixture was stirred at 50° C. for 4 hours
extractionthe mixture was extracted with ethyl acetate
washThe organic layer washed with an aqueous saturated sodium chloride solution
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-430b7853cbde4d4bb7935c2035fb6869
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07691883B2

Reaction notes

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