Sodium Iodide → t-Butyl methyl 7-iodoheptylmalonate

HRID 21987

Reaction equation

HRID 21987 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]([C:17]([O:19][CH3:20])=[O:18])[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].[I-:21].[Na+]>CC(C)=O>[I:21][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]([C:17]([O:19][CH3:20])=[O:18])[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 19930816t-Butyl methyl 7-bromoheptylmalonate

Product 1

HCID 19930825t-Butyl methyl 7-iodoheptylmalonate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

t-Butyl methyl 7-bromoheptylmalonate (8.81 g, 25.1 mmol) is dissolved in acetone (50 ml). Sodium iodide (3.7 g, 25.1 mmol) is added and the mixture is stirred at reflux for 2 hours. The reaction mixture is filtered and the filtrate is concentrated to dryness. The residue is dissolved in methylene chloride and filtered again. The filtrate is concentrated to dryness to give t-butyl methyl 7-iodoheptylmalonate as an oil.

Workup

  1. temperatureat reflux for 2 hours
  2. filtrationThe reaction mixture is filtered
  3. concentrationthe filtrate is concentrated to dryness
  4. dissolutionThe residue is dissolved in methylene chloride
  5. filtrationfiltered again
  6. concentrationThe filtrate is concentrated to dryness

Sources & evidence

ORD record
ord-b8ac2a8fbbd24551a35842c1f9e8fd6a
Source dataset
uspto-grants-1995_06
Patent number
US05426103

Linked notes

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