Water → 2,4-Dichlorophenyl 1-(3-pyridyl)-cyclopropyl ketone

HRID 1087403Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:17])[CH2:10][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1.[I-].Cl[CH2:20][CH2:21][S+](C)C.[I-].[Na+].O>C(O)(C)(C)C>[N:13]1[CH:14]=[CH:15][CH:16]=[C:11]([C:10]2([C:9]([C:3]3[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=3[Cl:1])=[O:17])[CH2:21][CH2:20]2)[CH:12]=1

Participants

Conditions

Temperature: 45 °C

Procedure

54 g of 2',4'-dichloro-2-(3-pyridyl)-acetophenone are added portionwise under an inert gas to a suspension of 46.5 g of freshly sublimed potassium tert.butylate in 590 ml of tert.butanol and the reaction mixture is stirred at 45° C. for 2 hours. The mixture is treated at room temperature with 59.5 g of 2-chloroethyl-dimethylsulphonium iodide and a spatula tip of sodium iodide and the mixture is held at 50° C. for 16 hours while stirring vigorously. The mixture is poured into water and extracted three times with 300 ml of diethyl ether each time. The combined organic extracts are washed with water, dried over anhydrous sodium sulphate and evaporated under reduced pressure. The residue is chromatographed on silica gel with diethyl ether as the eluent and crystallized from diethyl ether/n-hexane. There are obtained 41.7 g of 2,4-dichlorophenyl 1-(3-pyridyl)-cyclopropyl ketone as white crystals, m.p. 83° C.

Workup

stirringwhile stirring vigorously
extractionextracted three times with 300 ml of diethyl ether each time
washThe combined organic extracts are washed with water
dry with materialdried over anhydrous sodium sulphate
customevaporated under reduced pressure
customThe residue is chromatographed on silica gel with diethyl ether as the eluent
customcrystallized from diethyl ether/n-hexane

Sources & evidence

ORD record: ord-241d5b1d37f44a91bc2301947303c2fb
Source dataset: uspto-grants-1991_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05036074

Reaction notes

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