Methyl iodide → 4-methoxy-3-[3-[3-(2-hydroxyethoxy)phenyl]-1-oxo-2-propenyl]-1,6-dimethyl-2(1H)-pyridinone
Reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]([CH3:9])[C:4](=[O:10])[C:3]=1[C:11](=[O:24])[CH:12]=[CH:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH2:21][CH2:22][OH:23])[CH:15]=1.[H-].[Na+].I[CH3:28].S([O-])(O)(=O)=O.[Na+]>CN(C)C=O>[CH3:28][O:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]([CH3:9])[C:4](=[O:10])[C:3]=1[C:11](=[O:24])[CH:12]=[CH:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH2:21][CH2:22][OH:23])[CH:15]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a mixture of 1.41 g of 4-hydroxy-3-[3-[3-(2-hydroxyethoxy)phenyl]-1-oxo-2-propenyl]-1,6-dimethyl-2(1H)-pyridinone and 14 ml of dimethylformamide was added 0.19 g of sodium hydride (60% oily) under ice-cooling. After stirred at room temperature for 1 hour, 1.82 g of iodomethane was added, and this was stirred at room temperature to 42° C. for 5 hours. The reaction solution was neutralized with sodium hydrogen sulfate under ice-cooling, this was concentrated under reduced pressure, and the resulting residue was subjected to silica gel column chromatography to obtain 0.67 g of 4-methoxy-3-[3-[3-(2-hydroxyethoxy)phenyl]-1-oxo-2-propenyl]-1,6-dimethyl-2(1H)-pyridinone [Compound No. (41a)] as a yellow crystal.
Workup
- temperaturecooling
- stirringthis was stirred at room temperature to 42° C. for 5 hours
- temperaturecooling
- concentrationthis was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-df8400fdff49433097013c0cab41eaad
- Source dataset
- uspto-grants-2011_08
- Patent number
- US07989478B2
Reaction notes
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