HCID 10083993, compound → HCID 18427479, compound

HRID 1275160Notes

Reaction equation

HRID 1275160 reaction equation
[CH3:1]C(C)([O-])C.[K+].[Cl:7][C:8]1[CH:9]=[C:10]([C:15](=O)[CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH:11]=[CH:12][C:13]=1[Cl:14]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1C=CC=CC=1>[Cl:7][C:8]1[CH:9]=[C:10]([C:15](=[CH2:1])[CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH:11]=[CH:12][C:13]=1[Cl:14]

Participants

5

Reactant 2

HCID 10083993HCID 10083993, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 18427479HCID 18427479, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 241BenzeneSolvent2×

Procedure

330 mg (0.92 mmole) of methyltriphenylphosphonium bromide and 105 mg (0.94 mmole) of potassium t-butoxide were suspended in 4 ml of dried benzene, and the mixture was stirred under a stream of nitrogen at room temperature for 4 hours. A solution prepared by dissolving 200 mg of methyl 4-(3,4-dichlorophenyl)-4-oxobutanoate [prepared as described in step (a) above] in 1 ml of benzene was added to the reaction mixture, and the mixture was then stirred for 18 hours. At the end of this time, the reaction mixture was filtered through a Celite (trade mark) filter aid and washed with diethyl ether. The filtrate was then concentrated by evaporation under reduced pressure. The resulting residue was purified by silica gel column chromatography, using a 23:2 by volume mixture of hexane and diethyl ether as the eluent, to give 95 mg (yield 64%) of the title compound as a pale yellow oil.

Workup

  1. customA solution prepared
  2. additionwas added to the reaction mixture
  3. stirringthe mixture was then stirred for 18 hours
  4. filtrationAt the end of this time, the reaction mixture was filtered through a Celite (trade mark)
  5. filtrationfilter aid
  6. washwashed with diethyl ether
  7. concentrationThe filtrate was then concentrated by evaporation under reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography
  9. additionby volume mixture of hexane and diethyl ether as the eluent

Sources & evidence

ORD record
ord-f88aa8ac39b243fe8f2b5e21b4a49124
Source dataset
uspto-grants-2000_12
Patent number
US06159967

Reaction notes

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