Water → HCID 57392868, compound
Reaction equation
C(OP([CH2:9][C:10]#[N:11])(=O)OCC)C.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH2:22]([O:24][C:25]1[CH:26]=[C:27]([C:33]([C:35]2[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[C:37]([OH:43])[CH:36]=2)=O)[CH:28]=[CH:29][C:30]=1[O:31][CH3:32])[CH3:23].O>C1COCC1>[CH2:22]([O:24][C:25]1[CH:26]=[C:27](/[C:33](/[C:35]2[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[C:37]([OH:43])[CH:36]=2)=[CH:9]\[C:10]#[N:11])[CH:28]=[CH:29][C:30]=1[O:31][CH3:32])[CH3:23]Participants
Procedure
To a solution of cyanomethylphosphonic acid diethyl ester (8.1 mL, 51.6 mmol) in anhydrous THF (50 mL) was added lithium bis(trimethylsilyl)amide (1.0 M solution in THF, 51.6 mL, 51.6 mmol) at 0° C. and stirred for 30 min at room temperature followed by addition of (3-ethoxy-4-methoxy-phenyl)-(3-hydroxy-4-methoxy-phenyl)-methanone (5.20 g, 17.2 mmol) in THF (40 mL) and refluxed overnight. The reaction mixture was poured into water (50 mL), extracted with CH2Cl2 (2×60 mL). The combined organic phases were washed with brine (60 mL), dried over MgSO4, and purified via flash column chromatography (EtOAc/Hexane) to give E/Z-3-(3-ethoxy-4-methoxy-phenyl) -3-(3-hydroxy-4-methoxy-phenyl)-acrylonitrile as an off-white solid (5.26 g, 94% yield). The product was used in the next step without further purification.
Workup
- temperaturerefluxed overnight
- extractionextracted with CH2Cl2 (2×60 mL)
- washThe combined organic phases were washed with brine (60 mL)
- dry with materialdried over MgSO4
- custompurified via flash column chromatography (EtOAc/Hexane)
Sources & evidence
- ORD record
- ord-205c576255d544c9a7ccc33c6100aa9c
- Source dataset
- uspto-grants-2008_12
- Patent number
- US07470723B2
Reaction notes
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