Iodoethane → Ethyl 2-ethyl-3-oxopentanoate
Reaction equation
[CH2:1]([O:3][C:4](=[O:10])[CH2:5][C:6](=[O:9])[CH2:7][CH3:8])[CH3:2].[CH3:11][CH2:12][O-].[Na+].C(I)C>CCO>[CH2:1]([O:3][C:4](=[O:10])[CH:5]([CH2:11][CH3:12])[C:6](=[O:9])[CH2:7][CH3:8])[CH3:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a solution of 3-oxo-pentanoic acid ethyl ester (5.19 g, 36 mmol) in anhydrous EtOH (40 mL) was added NaOEt (21% wt. in EtOH, 11.7 mL, 36 mmol). he reaction mixture was heated to 80° C. Ethyl iodide (6.18 g, 39.6 mmol) was added dropwise at 80° C. Stirring was continued at 80° C. for 16 hours. The reaction mixture was concentrated and loaded onto a silica gel column and eluted with 1-2% EtOAc/heptane to give 4.38 g of the title compound.
Workup
- customhe reaction mixture
- concentrationThe reaction mixture was concentrated
- washeluted with 1-2% EtOAc/heptane
Sources & evidence
- ORD record
- ord-0ffbdf6f078b488cac34ea6b80427d20
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08642603B2
Reaction notes
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