Diethyl Ether → HCID 19073679, compound

HRID 376199Notes

Reaction equation

HRID 376199 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-a439ad0670e94df0b8c83c0a0128e1f5
Source dataset
uspto-grants-1996_01
Patent number
US05488149

Reaction notes

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