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

HRID 719123ノート

反応式

HRID 719123 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b409d5c049e44fc9b3ee480d00d8fc9b
出典データセット
uspto-grants-2006_11
特許番号
US07132421B2

反応ノート

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