Sodium Iodide → Ethyl 4-iodo-3-oxobutanoate

HRID 2226657Notes

Reaction equation

HRID 2226657 reaction equation
[I-:1].[Na+].Cl[CH2:4][C:5](=[O:12])[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8]>CC(C)=O.CCCCC.O.C(OCC)(=O)C>[I:1][CH2:4][C:5](=[O:12])[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

7

Reactant 2

HCID 5238Sodium Iodide2×HCID 69484Ethyl 4-chloroacetoacetate

Product 1

HCID 12779728Ethyl 4-iodo-3-oxobutanoate

Reagents, catalysts & solvents 4

HCID 180AcetoneSolventHCID 962WaterSolventHCID 8003PentaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Sodium iodide (228 g) was dissolved in acetone (135 mL) and cooled to 0° C. 4-chloro-3-oxobutanoic acid, ethyl ester (5.0 g) was added to the sodium iodide solution and the mixture was stirred at 0° C. for 20 minutes. It was diluted with pentane (135 mL) and water (135 mL). The reaction mixture was diluted with ethyl acetate and washed with water, brine and dried over anhydrous sodium sulfate to give an intermediate (4-Iodo-3-oxobutanoic acid, ethyl ester; 6.2 g yield).

Workup

  1. washwashed with water, brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customto give

Sources & evidence

ORD record
ord-31734ba6240e48b099acd4eb53137c50
Source dataset
uspto-grants-1994_09
Patent number
US05349069

Reaction notes

Loading…