Iodoethane → HCID 51381260, compound

HRID 2072829Notes

Reaction equation

HRID 2072829 reaction equation
[C:1]([O:6][CH2:7][CH3:8])(=[O:5])[C@H:2]([CH3:4])[OH:3].[CH2:9](I)[CH3:10]>[Ag]=O.CN(C=O)C>[CH2:9]([O:3][C@@H:2]([CH3:4])[C:1]([O:6][CH2:7][CH3:8])=[O:5])[CH3:10]

Participants

5

Reactant 2

HCID 6340IodoethaneHCID 92831(L)-ethyl lactate

Product 1

HCID 51381260HCID 51381260, compound

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 20 g of (s)-(-)-ethyl lactate, 100 ml of N,N'-dimethylformamide, 38 g of ethyl iodide and 30 g of silver oxide was stirred at room temperature for 40 hours. The insoluble materials were separated by filtration and water and hexane were added to the filtrate to separate N,N'-dimethylformamide. The aqueous layer was subsequently extracted twice with hexane, and the hexane layers were dried over anhydrous sodium sulfate. The product was distilled under reduced pressure to give 18.5 g of a fraction having a boiling point of 86°-88° C./75 mmHg. Nuclear magnetic resoanance spectroscopy led to the determination that this fraction was the desired product.

Workup

  1. customThe insoluble materials were separated by filtration and water and hexane
  2. additionwere added to the filtrate
  3. customto separate N,N'-dimethylformamide
  4. extractionThe aqueous layer was subsequently extracted twice with hexane
  5. dry with materialthe hexane layers were dried over anhydrous sodium sulfate
  6. distillationThe product was distilled under reduced pressure
  7. customto give 18.5 g of a fraction

Sources & evidence

ORD record
ord-480e0044fe624a3ea7a235c63ef8583c
Source dataset
uspto-grants-1990_04
Patent number
US04914224

Reaction notes

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