Iodoethane → methyl 3-(4-bromophenyl)-2(S)-ethoxypropanoate

HRID 910293Notes

Reaction equation

HRID 910293 reaction equation
[CH2:1](I)[CH3:2].[Br:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C@H:12]([OH:17])[C:13]([O:15][CH3:16])=[O:14])=[CH:7][CH:6]=1>C(OC(C)C)(C)C.[Ag-]=O.[Ag]=O>[Br:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:11][C@H:12]([O:17][CH2:1][CH3:2])[C:13]([O:15][CH3:16])=[O:14])=[CH:9][CH:10]=1

Participants

6

Reactant 2

HCID 6340Iodoethane2×HCID 39359925methyl (S)-3-(4-bromophenyl)-2-hydroxypropionate

Product 1

HCID 67148373methyl 3-(4-bromophenyl)-2(S)-ethoxypropanoateYield 79%

Reagents, catalysts & solvents 3

HCID 92152Silver(II) oxideCatalystHCID 178418778HCID 178418778, compoundCatalystHCID 7914Diisopropyl EtherSolvent

Conditions

Temperature
70 °C

Procedure

11 ml of ethyl iodide are added dropwise to a solution of 23.5 g (91 mmol) of methyl 3-(4-bromophenyl)-2(S)-hydroxypropanoate and 35.6 g (155 mmol) of silver(I) oxide in 120 ml of isopropyl ether. The reaction medium is heated at 70° C. overnight. 10 g (45 mmol) of silver oxide and 3.7 ml (45 mmol) of ethyl iodide are added and the reaction medium is heated for a further 4 hours and then filtered through Celite, the precipitate is rinsed with ethyl acetate and the filtrate is concentrated under vacuum. The residue obtained is purified by chromatography on a column of silica eluted with a 95/5 and then 90/10 heptane/ethyl acetate mixture. 20 g (79%) of methyl 3-(4-bromophenyl)-2(S)-ethoxypropanoate are obtained.

Workup

  1. temperaturethe reaction medium is heated for a further 4 hours
  2. filtrationfiltered through Celite
  3. washthe precipitate is rinsed with ethyl acetate
  4. concentrationthe filtrate is concentrated under vacuum
  5. customThe residue obtained
  6. customis purified by chromatography on a column of silica
  7. washeluted with a 95/5

Sources & evidence

ORD record
ord-b03b79b5dea449b9a644a4a33382949e
Source dataset
uspto-grants-2011_09
Patent number
US08022079B2

Reaction notes

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