Methyl Acrylate → 3-(4-Formyl-2,6-dimethyl-phenyl)-acrylic acid methyl ester
Reaction equation
[CH:1]([C:3]1[CH:8]=[C:7]([CH3:9])[C:6](OS(C(F)(F)F)(=O)=O)=[C:5]([CH3:18])[CH:4]=1)=[O:2].C(N(CC)CC)C.[C:26]([O:30][CH3:31])(=[O:29])[CH:27]=[CH2:28]>CN(C=O)C.C(OCC)C.CC([O-])=O.CC([O-])=O.[Pd+2].C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:31][O:30][C:26](=[O:29])[CH:27]=[CH:28][C:6]1[C:7]([CH3:9])=[CH:8][C:3]([CH:1]=[O:2])=[CH:4][C:5]=1[CH3:18]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 115 °C
Procedure
To a stirred solution of trifluoro-methanesulfonic acid 4-formyl-2,6-dimethyl-phenyl ester (4.7 g, 16.7 mmol) in dry DMF (75 mL) under argon is sequentially added at rt triethylamine (3.4 g, 33.3 mmol), methyl acrylate (14.3 g, 167 mmol), 1,3-bis-(diphenylphosphino)-propane (378 mg, 0.92 mmol) and Pd(OAc)2 (187 mg, 0.83 mmol). The mixture is heated to 115° C. and stirred for 5 h. The mixture is diluted with diethyl ether (350 mL) and washed twice with aq. 1 N HCl and once with sat. aq. NaHCO3. The organic extract is dried over MgSO4, filtered and evaporated. The residue is purified by CC on silica gel eluting with heptane:EA 5:1 to give 3-(4-formyl-2,6-dimethyl-phenyl)-acrylic acid methyl ester (2.9 g) as a slightly yellow solid; LC-MS: tR=0.96 min.
Workup
- washwashed twice with aq. 1 N HCl and once with sat. aq. NaHCO3
- extractionThe organic extract
- dry with materialis dried over MgSO4
- filtrationfiltered
- customevaporated
- customThe residue is purified by CC on silica gel eluting with heptane:EA 5:1
Sources & evidence
- ORD record
- ord-62028ba17af4459d848031701abf3eac
- Source dataset
- uspto-grants-2011_10
- Patent number
- US08039644B2
Reaction notes
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