Water → Ethyl 2-pyridin-3-ylpropanoate
Reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:2]=1.[Li+].[CH3:14]C([N-]C(C)C)C.O.CCOCC>C1COCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]([CH3:14])[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:2]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Ethyl 3-pyridylacetate (12.2 g, 73.9 mmol) in THF (30 ml) was added to LDA (81 mmol) in THF (150 ml) over 10 min at -78° C. After 1 h Mel (5.1 ml, 81 mmol) was added to the yellow suspension and the mixture brought to room temperature. H2O (300 ml) and ether (300 ml) was added, the mixture separated, and the organic layer washed with H2O and brine, dried and evaporated to give ethyl 2-(3-pyridyl)propanoate (8.3 g) as a yellow oil.
Workup
- additionAfter 1 h Mel (5.1 ml, 81 mmol) was added to the yellow suspension
- custombrought to room temperature
- customthe mixture separated
- washthe organic layer washed with H2O and brine
- customdried
- customevaporated
Sources & evidence
- ORD record
- ord-e1e67158406e495f8ce377dc45162e4c
- Source dataset
- uspto-grants-1999_11
- Patent number
- US05977116
Reaction notes
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