Ethyl Acrylate → 3-[3-(1-Amino-1-methyl-ethyl)-phenyl]-2-methylacrylic acid methyl ester
Reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]([NH2:11])([CH3:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1.CN([CH:20]1[CH2:25][CH2:24]CCC1)C1CCCCC1.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.[C:39]([O:43][CH2:44]C)(=[O:42])C=C>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O.O1CCOCC1>[CH3:44][O:43][C:39](=[O:42])[C:25]([CH3:24])=[CH:20][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([NH2:11])([CH3:10])[CH3:9])[CH:3]=1Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 80 °C
Procedure
The mixture of 1-(3-bromo-phenyl)-1-methyl-ethylamine (0.74 g, 3.5 mmol), tris(dibenzylideneacetone)dipalladium (0.19 g, 0.21 mmol), and N-methyldicyclohexylamine (10 mmol) was purged with nitrogen followed by the addition of 1,4-dioxane (7 mL) and tri-tert-butylphospine (85 mg, 0.42 mmol). The mixture was again purged with nitrogen and ethyl acrylate (0.75 mL, 7.0 mmol) was added. The mixture was heated to 80° C. for 1 h, brought to room temperature, poured into water (50 mL) and extracted with ethyl acetate (100 mL). The organic layer was separated, washed again with water, dried over magnesium sulfate, concentrated and chromatographed on silica gel using 0-4% MeOHI/CH2Cl2 to afford yellow oil.
Workup
- customwas purged with nitrogen
- additionwas added
- custombrought to room temperature
- extractionextracted with ethyl acetate (100 mL)
- customThe organic layer was separated
- washwashed again with water
- dry with materialdried over magnesium sulfate
- concentrationconcentrated
- customchromatographed on silica gel using 0-4% MeOHI/CH2Cl2
- customto afford yellow oil
Sources & evidence
- ORD record
- ord-82f70b5da0c44140bd1eb2eb0d078c06
- Source dataset
- uspto-grants-2009_03
- Patent number
- US07504403B2
Reaction notes
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