Sodium Iodide → Methyl cis-7-Iodo-5-heptenoate

HRID 34717Notes

Reaction equation

HRID 34717 reaction equation
Br[CH2:2]/[CH:3]=[CH:4]\[CH2:5][CH2:6][CH2:7][C:8]([O:10][CH3:11])=[O:9].C(=O)([O-])[O-].[Na+].[Na+].[I-:18].[Na+].O1CCCC1>CC(C)=O.CCOCC>[I:18][CH2:2]/[CH:3]=[CH:4]\[CH2:5][CH2:6][CH2:7][C:8]([O:10][CH3:11])=[O:9]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 8028TetrahydrofuranHCID 10340Sodium Carbonate2×HCID 11253002Methyl cis-7-bromo-5-heptenoate

Product 1

HCID 11076425Methyl cis-7-Iodo-5-heptenoate

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 31.4 g of cis-7-bromo-5-heptenoic acid, methyl ester in 260 ml of acetone, containing a trace of sodium carbonate was added a solution of 24.7 g of sodium iodide in 260 ml of acetone. A precipitate formed immediately. After 2 minutes, the solution was diluted with 850 ml of ether and filtered. A trace of sodium carbonate was added to the filtrate which was then stripped, redissolved in ether, refiltered, sodium carbonate added and the filtrate stripped, giving 37.9 g of light sensitive product. This product was stored in the cold as a 1M solution in either ether or tetrahydrofuran containing a trace of sodium carbonate and protected from the light. NMR: 5.95-5.2 ppm (2H, m, olefins), 3.85 ppm (2H, d, 7 Hz, ICH2), 3.65 ppm (3H, s, OMe), 2.45-2.0 ppm (4H, m, CH2 --CH2), 1.8 ppm (2H, q, 7 Hz, CH2).

Workup

  1. customA precipitate formed immediately
  2. filtrationfiltered
  3. additionA trace of sodium carbonate was added to the filtrate which
  4. dissolutionredissolved in ether
  5. additionsodium carbonate added
  6. customgiving 37.9 g of light sensitive product

Sources & evidence

ORD record
ord-9e0796f10ee942e7a5b606ad98ad593b
Source dataset
uspto-grants-1988_08
Patent number
US04762935

Reaction notes

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