Tetrahydrofuran → Ethyl 2-methyl-3-(3'-methylaminobiphenyl-4-yl)acrylate
Reaction equation
[H-].[Na+].[CH3:3][NH:4][C:5]1[CH:6]=[C:7]([C:11]2[CH:16]=[CH:15][C:14]([CH:17]=O)=[CH:13][CH:12]=2)[CH:8]=[CH:9][CH:10]=1.[Cl-].[NH4+].[C:21]([O:24][CH2:25][CH3:26])(=[O:23])[CH3:22].O1CCC[CH2:28]1>>[CH3:28][C:22](=[CH:17][C:14]1[CH:13]=[CH:12][C:11]([C:7]2[CH:8]=[CH:9][CH:10]=[C:5]([NH:4][CH3:3])[CH:6]=2)=[CH:16][CH:15]=1)[C:21]([O:24][CH2:25][CH3:26])=[O:23]Participants
Conditions
- Temperature
- 0 °C
Procedure
At 0° C., a solution of 1.6 mL (9.5 mmol) of triethyl phosphonopropionate in 5 mL of tetrahydrofuran is added to a suspension of 379 mg (9.5 mmol) of sodium hydride in 5 mL of tetrahydrofuran. The mixture is stirred for 15 minutes at 0° C. and a solution of 800 mg (3.8 mmol) of 3′-methylaminobiphenyl-4-carbaldehyde in 5 mL of tetrahydrofuran is then added. The reaction mixture is stirred for 12 hours at room temperature. The reaction is worked up by addition of 50 mL of saturated ammonium chloride solution and extraction with ethyl acetate. The organic phases are washed with sodium chloride solution and dried over magnesium sulfate. The solvents are evaporated off, and the residue is then purified by chromatography on a column of silica eluted with a 7/3 heptane/ethyl acetate mixture. 750 mg (67%) of ethyl 2-methyl-3-(3′-methylaminobiphenyl-4-yl)acrylate, (E) isomer, are obtained.
Workup
- stirringThe reaction mixture is stirred for 12 hours at room temperature
- washThe organic phases are washed with sodium chloride solution
- dry with materialdried over magnesium sulfate
- customThe solvents are evaporated off
- customthe residue is then purified by chromatography on a column of silica
- washeluted with a 7/3 heptane/ethyl acetate mixture
Sources & evidence
- ORD record
- ord-77a06f07f7184a9987aa881ba6f64cfc
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08383652B2
Reaction notes
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