Dimethyl Sulfate → HCID 54564688, compound
Reaction equation
[H-].[Na+].[OH:3][C:4](=[C:16]([C:19]#[N:20])[C:17]#[N:18])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][CH3:15])[CH:7]=1.S(OC)(O[CH3:25])(=O)=O>C1COCC1>[CH3:25][O:3][C:4](=[C:16]([C:17]#[N:18])[C:19]#[N:20])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][CH3:15])[CH:7]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To 60% NaH (5.7 g, 0.14 mol) in THF (150 ml) at -78° C. under argon was added dropwise (1-hydroxy-(3,4-dimethoxyphenylethylidene))malononitrile (34.6 g, 0.14 mol) in THF (100 ml) over 1.25 hours. The reaction mixture was stirred for 2 hours and dimethyl sulfate (26.9 g, 0.21 mol) in THF (50 ml) was added over 30 minutes. The reaction mixture was warmed to room temperature and stirred for 24 hours. The solvents were removed in vacuo and the residue was partitioned between ether and water. The organic layer was separated and the aqueous layer was extracted with ether (3×150 ml). The ether layers were combined and the solvent was removed in vacuo. The residue was purified by column chromatography on silica gel eluting with hexane/ether (6/4) to afford crude (1-methoxy-(3,4-dimethoxyphenylethylidene))malononitrile as a gold oil.
Workup
- stirringstirred for 24 hours
- customThe solvents were removed in vacuo
- customthe residue was partitioned between ether and water
- customThe organic layer was separated
- extractionthe aqueous layer was extracted with ether (3×150 ml)
- customthe solvent was removed in vacuo
- customThe residue was purified by column chromatography on silica gel eluting with hexane/ether (6/4)
Sources & evidence
- ORD record
- ord-3e501cbd9bfa498cbda045041193f282
- Source dataset
- uspto-grants-1994_03
- Patent number
- US05294612
Reaction notes
Loading…