Water → 1-(4-Chloro-phenyl)-3-cyclopentyl-propan-1-one

HRID 719123Notes

Reaction equation

[Cl-].[Al+3].[Cl-].[Cl-].[CH:5]1([CH2:10][CH2:11][C:12](Cl)=[O:13])[CH2:9][CH2:8][CH2:7][CH2:6]1.[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O>ClCCCl>[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([C:12](=[O:13])[CH2:11][CH2:10][CH:5]2[CH2:9][CH2:8][CH2:7][CH2:6]2)=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Aluminum chloride (4.979 g, 37.34 mmol) was added in small portions to a solution of 3-cyclopentylpropionyl chloride (3 g, 18.67 mmol) in 1,2-dichloroethane (100 mL) cooled to 0° C. After 15 min., chlorobenzene (6.304 g, 56.01 mmol) was added. The reaction mixture was stirred at 0° C. for 1 h and at room temperature for 48 h. It was then poured into a mixture of ice and water. The product was extracted with ethyl acetate. The organic layers were washed with saturated solution of sodium bicarbonate (1×30 mL), brine (1×20 mL) and dried over anhydrous magnesium sulfate. The solids were then filtered off, and the filtrate was concentrated in vacuo. Purification of the crude residue by flash chromatography (Biotage system, KP-Sil™ 32–63 μm, 60 Å silica gel) eluting with hexanes yielded 1-(4-chloro-phenyl)-3-cyclopentyl-propan-1-one (1.12 g, 25%) as yellow oil.

Workup

extractionThe product was extracted with ethyl acetate
washThe organic layers were washed with saturated solution of sodium bicarbonate (1×30 mL), brine (1×20 mL)
dry with materialdried over anhydrous magnesium sulfate
filtrationThe solids were then filtered off
concentrationthe filtrate was concentrated in vacuo
customPurification of the crude residue by flash chromatography (Biotage system, KP-Sil™ 32–63 μm, 60 Å silica gel)
washeluting with hexanes

Sources & evidence

ORD record: ord-b409d5c049e44fc9b3ee480d00d8fc9b
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07132421B2

Reaction notes

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