Sodium hydride → Methyl 3-[(4-chlorophenyl)carbonyl]-4-oxopentanoate

HRID 563993

反応式

HRID 563993 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:13])[CH2:9][C:10](=[O:12])[CH3:11])=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:17][C:18]([O:20][CH3:21])=[O:19]>CS(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([CH:9]([C:10](=[O:12])[CH3:11])[CH2:17][C:18]([O:20][CH3:21])=[O:19])=[O:13])=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 2380831-(4-Chlorophenyl)butane-1,3-dione

生成物 1

HCID 67004944Methyl 3-[(4-chlorophenyl)carbonyl]-4-oxopentanoate収率 56.7%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒3 回

反応条件

温度
20 °C

実験手順

A solution of 10 g (51 mmol) of 1-(4-chlorophenyl)butane-1,3-dione (commercially available) dissolved in dimethyl sulfoxide was slowly added dropwise to 2.237 g (56 mmol) of sodium hydride in 200 ml of dimethyl sulfoxide such that the temperature did not exceed 30° C. The mixture was stirred at 20° C. for another 30 minutes. 8.558 g (56 mmol) of methyl bromoacetate in a little dimethyl sulfoxide were then slowly added dropwise at 0° C. The mixture was stirred at 20° C. for 4 hours. The reaction mixture was poured into ice-water and extracted with dichloromethane. The organic phase was repeatedly washed with water. Drying of the combined organic phases, removal of the solvent under reduced pressure and chromatography of the residue gave 7.750 g of product (56.7% of theory); NMR (CDCl3, 400 MHz): 2.19 (s, 3H); 2.99 (d, 1H); 3.03 (d, 1H); 3.69 (s, 3H); 4.95 (dd, 1H); 7.49 (d, 2H); 7.98 (d, 2H).

後処理

  1. customdid not exceed 30° C
  2. stirringThe mixture was stirred at 20° C. for 4 hours
  3. extractionextracted with dichloromethane
  4. washThe organic phase was repeatedly washed with water
  5. customDrying of the combined organic phases, removal of the solvent under reduced pressure and chromatography of the residue

出典と根拠

ORDレコード
ord-6a0aab01bf2c4aba867bb4403f77b4bc
出典データセット
uspto-grants-2011_11
特許番号
US08067611B2

関連ノート

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