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

HRID 719123노트

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HRID 719123 반응식
[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

참가 물질

6

반응물 4

HCID 962WaterHCID 7964ChlorobenzeneHCID 660393-Cyclopentylpropionyl chlorideHCID 6451240Aluminum(III) Chloride

생성물 1

HCID 218969001-(4-Chloro-phenyl)-3-cyclopentyl-propan-1-one수율 25.3%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

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온도
0 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-b409d5c049e44fc9b3ee480d00d8fc9b
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07132421B2

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