Diisopropylethylamine → 2-((Methoxy)(4-phenoxyphenyl)methylene)malononitrile
Reaction equation
[C:1]([C:3]([C:19]#[N:20])=[C:4]([OH:18])[C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:7][CH:6]=1)#[N:2].[CH:21](N(C(C)C)CC)(C)C.C[Si](C=[N+]=[N-])(C)C>C(#N)C.CO.C1COCC1>[C:1]([C:3]([C:19]#[N:20])=[C:4]([O:18][CH3:21])[C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[CH:7][CH:6]=1)#[N:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 20 °C
Procedure
1,1-Dicyano-2-hydroxy-2-(4-phenoxyphenyl)ethene (56.5 g) in acetonitrile (780 mL) and methanol (85 mL) is stirred under nitrogen at 0° C. while adding diisopropylethylamine (52.5 mL) followed by 2M trimethylsilyldiazomethane (150 mL) in THF. The reaction is stirred for 2 days at 20° C., and then 2 g of silica is added (for chromatography). The brown-red solution is evaporated in vacuo, the residue dissolved in ethyl acetate and washed well with water then brine, dried and evaporated. The residue is extracted with diethyl ether (3×250 mL), decanting from insoluble oil. Evaporation of the ether extracts gives 22.5 g of 1,1-dicyano-2-methoxy-2-(4-phenoxyphenyl)ethene as a pale orange solid. The insoluble oil is purified by flash chromatography to give 15.0 g of a red-orange oil.
Workup
- addition2 g of silica is added (for chromatography)
- customThe brown-red solution is evaporated in vacuo
- dissolutionthe residue dissolved in ethyl acetate
- washwashed well with water
- dry with materialbrine, dried
- customevaporated
- extractionThe residue is extracted with diethyl ether (3×250 mL)
- customdecanting from insoluble oil
- customEvaporation of the ether
Sources & evidence
- ORD record
- ord-d8f20f2aefa84829b115d7c6ed68987b
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07732454B2
Reaction notes
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