Diisopropyl Ether → HCID 9971622, compound

HRID 1708398Notes

Reaction equation

HRID 1708398 reaction equation
[O:1]=[C:2]([CH2:9][CH2:10][CH3:11])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[N+:12]([C:15]1[CH:22]=[CH:21][C:18]([CH2:19]Br)=[CH:17][CH:16]=1)([O-:14])=[O:13].[Cl-].[Li+].C(N(C(C)C)CC)(C)C.C(OC(C)C)(C)C>O1CCCC1.[Hg]>[N+:12]([C:15]1[CH:22]=[CH:21][C:18]([CH2:19][CH:3]([C:2](=[O:1])[CH2:9][CH2:10][CH3:11])[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[CH:17][CH:16]=1)([O-:14])=[O:13]

Participants

8

Reactant 5

HCID 7914Diisopropyl EtherHCID 660114-Nitrobenzyl bromideHCID 81531DiisopropylethylamineHCID 238498Ethyl 3-oxohexanoateHCID 433294Lithium Chloride

Product 1

HCID 9971622HCID 9971622, compoundYield 73.5%

Reagents, catalysts & solvents 2

HCID 23931MercuryCatalystHCID 8028TetrahydrofuranSolvent

Procedure

127.7 g of ethyl 3-oxohexanoate are dissolved in 700 ml of tetrahydrofuran. 174.5 g of 4-nitrobenzyl bromide and 35 g of lithium chloride are added and the mixture is stirred at room temperature. 286 ml of diisopropylethylamine are then introduced dropwise, which causes a slight exothermic effect. The mixture is then stirred for 3 hours at room temperature and thereafter for 10 hours under reflux. The solvents are evaporated off under vacuum and the residue is taken up with water and then extracted with chloroform. The organic phase is separated after settling has taken place and then washed with dilute hydrochloric acid solution, dried over magnesium sulphate and evaporated under vacuum. The oily residue obtained is taken up with isopropyl ether and the crystals formed are filtered off. The mother liquors are concentrated under vacuum and the residue is heated to 130° C. at 20 mmol mercury in order to remove the residual starting materials. 174 g of ethyl 2-(4-nitrobenzyl)-3-oxohexanoate are thereby obtained in the form of an oil, which is used without further purification for the next step.

Workup

  1. stirringThe mixture is then stirred for 3 hours at room temperature
  2. temperaturefor 10 hours under reflux
  3. customThe solvents are evaporated off under vacuum
  4. extractionextracted with chloroform
  5. customThe organic phase is separated after settling
  6. washwashed with dilute hydrochloric acid solution
  7. dry with materialdried over magnesium sulphate
  8. customevaporated under vacuum
  9. customThe oily residue obtained
  10. customthe crystals formed
  11. filtrationare filtered off
  12. concentrationThe mother liquors are concentrated under vacuum
  13. customto remove the

Sources & evidence

ORD record
ord-9e5431761f0046e9a90d585b9d5ddb0c
Source dataset
uspto-grants-1994_10
Patent number
US05358950

Reaction notes

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