Hydrochloric Acid → Ethyl-3-iodomethyl-4-iodobutyrate

HRID 377137Notes

Reaction equation

HRID 377137 reaction equation
[I:1][CH2:2][CH:3]([CH2:8][I:9])[CH2:4][C:5]([OH:7])=[O:6].Cl.[CH2:11](O)[CH3:12]>>[CH2:11]([O:6][C:5](=[O:7])[CH2:4][CH:3]([CH2:8][I:9])[CH2:2][I:1])[CH3:12]

Participants

4

Procedure

A solution of 2.831 g (8 mmole) 3-iodomethyl-4-iodobutyric acid 17 in 80 mL ethanol is saturated with HCl gas at 0° C. After stirring the solution at room temperature for two days, the solvent is removed under vacuum and the residue is dissolved in dichloromethane. The dichloromethane layer is washed with 10% aqueous sodium bicarbonate (3×100 mL), water (1×100 mL) and brine. The separated dichloromethane layer is dried over with magnesium sulfate, filtered and evaporated to give ethyl-3-iodomethyl-4-iodobutyrate 18.

Workup

  1. customthe solvent is removed under vacuum
  2. dissolutionthe residue is dissolved in dichloromethane
  3. washThe dichloromethane layer is washed with 10% aqueous sodium bicarbonate (3×100 mL), water (1×100 mL) and brine
  4. dry with materialThe separated dichloromethane layer is dried over with magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-d9ee218ebf4c4edcbb3f20ca6b21305e
Source dataset
uspto-grants-2000_02
Patent number
US06024937

Reaction notes

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