Sodium Iodide → Propanoic acid, 2-methyl-, 1-iodoethyl ester

HRID 1019171Notes

Reaction equation

HRID 1019171 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

HCID 5238Sodium IodideHCID 131387431-Chloroethyl 2-methylpropanoate

Product 1

HCID 14633820Propanoic acid, 2-methyl-, 1-iodoethyl esterYield 45.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

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

  1. filtrationThe orange suspension was filtered
  2. customthe filtrate was evaporated to dryness
  3. dissolutionThe crude product was dissolved in Et2O/H2O
  4. washthe organic phase was washed with aqueous sodium metabisulfite and brine
  5. dry with materialAfter drying (MgSO4)
  6. filtrationfiltering
  7. customremoval of solvent

Sources & evidence

ORD record
ord-94e4cba280d846c698823ff719093957
Source dataset
uspto-grants-2002_11
Patent number
US06486142B2

Reaction notes

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