Water → Ethyl 2-pyridin-3-ylpropanoate

HRID 1600840Notes

Reaction equation

HRID 1600840 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]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 96490Ethyl 3-pyridylacetateHCID 2724682Lithium diisopropylamide

Product 1

HCID 10726035Ethyl 2-pyridin-3-ylpropanoateYield 62.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

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

  1. additionAfter 1 h Mel (5.1 ml, 81 mmol) was added to the yellow suspension
  2. custombrought to room temperature
  3. customthe mixture separated
  4. washthe organic layer washed with H2O and brine
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-e1e67158406e495f8ce377dc45162e4c
Source dataset
uspto-grants-1999_11
Patent number
US05977116

Reaction notes

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