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

HRID 2351800Notes

Reaction equation

HRID 2351800 reaction equation
Br[CH2:2]/[CH:3]=[CH:4]\[CH2:5][CH2:6][CH2:7][C:8]([O:10][CH3:11])=[O:9].[Na+].[I-:13]>CC(C)=O>[I:13][CH2:2]/[CH:3]=[CH:4]\[CH2:5][CH2:6][CH2:7][C:8]([O:10][CH3:11])=[O:9]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 11253002Methyl cis-7-bromo-5-heptenoate

Product 1

HCID 11076425Methyl cis-7-Iodo-5-heptenoateYield 100.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of bromide 40 (0.29 g, 1.30 mmol) in dry acetone (10 mL) was added NaI (0.26 g, 1.70 mmol). The reaction mixture was stirred for 5 min, filtered, and poured into Et2O (50 mL) and water (20 mL). The ether layer was separated, washed with three 20-mL portions of water, dried over Na2SO4, and concentrated by rotary evaporation to yield the iodide 34 (0.35 g, 100%). The iodide was used immediately without further purification. If the reaction mixture was stirred for longer than 5 min, isomerization of the cis- to the transallyl iodide began to take place.

Workup

  1. filtrationfiltered
  2. additionpoured into Et2O (50 mL) and water (20 mL)
  3. customThe ether layer was separated
  4. washwashed with three 20-mL portions of water
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-d636f56283b740d694f6ebb71580d864
Source dataset
uspto-grants-1989_10
Patent number
US04873360

Reaction notes

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