Water → 3-Ethyl-4-nitrophenylacetic acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1)[CH3:2].[CH2:16]([Mg]Cl)[CH3:17].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.O>O1CCCC1>[CH2:1]([O:3][C:4](=[O:15])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[C:8]([CH2:16][CH3:17])[CH:7]=1)[CH3:2]Participants
Procedure
To a solution of 4-nitrophenylacetic acid ethyl ester (1.63 g) in tetrahydrofuran (100 mL) was dropwise added 2M ethyl magnesium chloride in tetrahydrofuran (3 mL) at −15° C. under argon atmosphere, and the mixture was stirred at the same temperature for 30 minutes. After further dropwise addition of 2M ethyl magnesium chloride in tetrahydrofuran (3 mL), the mixture was stirred at −15° C. for one hour, and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (3.0 g) was added thereto at the same temperature. The mixture was stirred overnight, and water (300 mL) was added thereto, followed by extraction with chloroform (150 mL×3). The organic layers were combined, washed with saturated brine, dried over sodium sulfate and purified by column chromatography on silica gel with hexane:ethyl acetate=10:1 to give the title compound (1.09 g).
Workup
- customat −15° C.
- stirringthe mixture was stirred at −15° C. for one hour
- stirringThe mixture was stirred overnight
- extractionfollowed by extraction with chloroform (150 mL×3)
- washwashed with saturated brine
- dry with materialdried over sodium sulfate
- custompurified by column chromatography on silica gel with hexane
Sources & evidence
- ORD record
- ord-84a444714f5a47b4bed520ff060b70bf
- Source dataset
- uspto-grants-2009_05
- Patent number
- US07538140B2
Reaction notes
Loading…