Sodium Iodide → Propanoic acid, 2-methyl-, 1-iodoethyl ester
Reaction equation
Cl[CH:2]([O:4][C:5](=[O:9])[CH:6]([CH3:8])[CH3:7])[CH3:3].[Na+].[I-:11]>CC#N>[I:11][CH:2]([O:4][C:5](=[O:9])[CH:6]([CH3:8])[CH3:7])[CH3:3]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of the chloro compound from Step 1 (2.6 g, 17.3 mmol) in CH3CN (20 mL) at r.t. was added NaI (2.85 g, 19 mmol). The flask was covered with Al foil and the reaction was stirred ON at r.t. The orange suspension was filtered and the filtrate was evaporated to dryness. The crude product was dissolved in Et2O/H2O and the organic phase was washed with aqueous sodium metabisulfite and brine. After drying (MgSO4), filtering, and removal of solvent, a pale brown oil (1.92 g) was obtained.
Workup
- filtrationThe orange suspension was filtered
- customthe filtrate was evaporated to dryness
- dissolutionThe crude product was dissolved in Et2O/H2O
- washthe organic phase was washed with aqueous sodium metabisulfite and brine
- dry with materialAfter drying (MgSO4)
- filtrationfiltering
- customremoval of solvent
Sources & evidence
- ORD record
- ord-94e4cba280d846c698823ff719093957
- Source dataset
- uspto-grants-2002_11
- Patent number
- US06486142B2
Reaction notes
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