Hydrochloric Acid → HCID 49886450, compound
Reaction equation
[C:1](#[N:3])[CH3:2].C([Li])CCC.[CH3:9][O:10][C:11]1[CH:20]=[C:19]([CH3:21])[CH:18]=[CH:17][C:12]=1[C:13](OC)=[O:14].Cl>C1COCC1>[CH3:9][O:10][C:11]1[CH:20]=[C:19]([CH3:21])[CH:18]=[CH:17][C:12]=1[C:13](=[O:14])[CH2:2][C:1]#[N:3]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a solution of acetonitrile (3.24 mL; 61.7 mmol) in dry THF (31 mL) at −78° C. under nitrogen atmosphere was added n-butyllithium 2.5M (15.4 mL; 38.5 mmol) and the reaction mixture was stirred at −78° C. for 30 minutes. Then, a solution of methyl 2-methoxy-4-methylbenzoate (2.78 g; 15.4 mmol) in dry THF (18 mL) was added dropwise and the stirring was continued for 1.5 hour. The reaction mixture was hydrolyzed by adding HCl (1N) and the aqueous layer was extracted several times with ethyl acetate. The organics were combined, dried over magnesium sulphatesulphate and concentrated under reduced pressure. The crude material was purified by flash chromatography on silica gel using a gradient of ethyl acetate (5 to 80%) in heptane to furnish 2.5 g of the expected 3-(2-methoxy-4-methylphenyl)-3-oxopropanenitrile (86%) as a bright yellow solid.
Workup
- waitthe stirring was continued for 1.5 hour
- extractionthe aqueous layer was extracted several times with ethyl acetate
- dry with materialdried over magnesium sulphatesulphate
- concentrationconcentrated under reduced pressure
- customThe crude material was purified by flash chromatography on silica gel using a gradient of ethyl acetate (5 to 80%) in heptane
Sources & evidence
- ORD record
- ord-37575900cb404a37b424616d28e86d6f
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08785638B2
Reaction notes
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