Diethyl Ether → HCID 19073679, compound

HRID 52869Notes

Reaction equation

HRID 52869 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH:10]([C:18](=[O:20])[CH3:19])[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:4][CH:3]=1.[Cl:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26]Cl)=[CH:24][CH:23]=1.CC(C)([O-])C.[K+].C(OCC)C>C(O)(C)(C)C.O>[Cl:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26][C:10]([CH2:9][CH2:8][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)([C:18](=[O:20])[CH3:19])[C:11]([O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:12])=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 19073714HCID 19073714, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 19073679HCID 19073679, compoundYield 321.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

1.94 g of tert-butyl 2-{2-(4-chlorophenyl)ethyl}-3-oxobutanoate was dissolved in 10 ml of tert-butanol, and 0.17 g of p-chlorobenzyl chloride and 0.90 g of potassium tert-butoxide were added thereto. The mixture was heated and refluxed for 1 hour. Then, ethyl ether and water were added to the reaction solution for liquid separation. The organic layer was washed with a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The drying agent was separated by filtration and then the solvent was distilled off under reduced pressure. The residue was subjected to medium pressure liquid chromatography (hexane/ethyl acetate=9/1) to obtain 1.43 g (yield: 52%) of tert-butyl 2-(4-chlorobenzyl)-2-{2-(4-chlorophenyl)ethyl}-3-oxobutanoate.

Workup

  1. temperatureThe mixture was heated
  2. temperaturerefluxed for 1 hour
  3. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe drying agent was separated by filtration
  6. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-15f7398109e540408fe773c29bc53ed2
Source dataset
uspto-grants-1997_04
Patent number
US05616803

Reaction notes

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