Dimethyl Sulfate → 4-methoxy-3-[3-[3-(cyanomethoxy)phenyl]-1-oxo-2-propenyl]-2H-1-benzopyran-2-one
Reaction equation
[OH:1][C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[O:5][C:4](=[O:12])[C:3]=1[C:13](=[O:26])[CH:14]=[CH:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH2:23][C:24]#[N:25])[CH:17]=1.[H-].[Na+].S(OC)(O[CH3:33])(=O)=O>>[CH3:33][O:1][C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[O:5][C:4](=[O:12])[C:3]=1[C:13](=[O:26])[CH:14]=[CH:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH2:23][C:24]#[N:25])[CH:17]=1Participants
Procedure
To a mixture of 5 ml of hexamethylphosphoramine and 0.40 g of 4-hydroxy-3-[3-[3-(cyanomethoxy)phenyl]-1-oxo-2-propenyl]-2H-1-benzopyran-2-one was added 52 mg of sodium hydride (60% oily), and the mixture was stirred at room temperature for 1 hour. Then, 0.17 g of dimethyl sulfate was added, and the mixture was stirred at room temperature overnight. 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 with anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 81 mg of 4-methoxy-3-[3-[3-(cyanomethoxy)phenyl]-1-oxo-2-propenyl]-2H-1-benzopyran-2-one [Compound No. (15d)] as a pale yellow crystal.
Workup
- stirringthe mixture was stirred at room temperature overnight
- extractionthe mixture was extracted with ethyl acetate
- washThe organic layer washed with an aqueous saturated sodium chloride solution
- dry with materialdried with anhydrous magnesium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-05129d0c8006472583bed4bb4f5f857d
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07691883B2
Reaction notes
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