Dimethyl Sulfoxide → 2-(3-Methoxyphenyl)cyclopentan-1-one

HRID 377306

反応式

HRID 377306 の反応式
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH:12]1[CH2:16][CH2:15][CH2:14][CH:13]1[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:24][O:23][C:19]1[CH:18]=[C:17]([CH:13]2[CH2:14][CH2:15][CH2:16][C:12]2=[O:11])[CH:22]=[CH:21][CH:20]=1

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 27596482-(3-Methoxyphenyl)-cyclopentanol

生成物 1

HCID 123629382-(3-Methoxyphenyl)cyclopentan-1-one収率 69.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

To a solution of oxalic chloride (9.0 ml) in methylene chloride (200 ml) was added dimethyl sulfoxide (9.6 ml) at -78° C. After 10 minutes, to the solution was added a solution of 1-hydroxy-2-(3-methoxyphenyl)cyclopentane (13 g) in methylene chloride (20 ml) at the same temperature. After 15 minutes, to the mixture was added triethylamine at -78° C. and the mixture was warmed at 0° C. for 1 hour. The reaction mixture was washed with water and brine and dried over magnesium sulfate. The organic solution was concentrated and the residue was purified by column chromatography on silica gel to give 2-(3-methoxyphenyl)cyclopentanone (8.9 g).

後処理

  1. waitAfter 15 minutes
  2. washThe reaction mixture was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationThe organic solution was concentrated
  5. customthe residue was purified by column chromatography on silica gel

出典と根拠

ORDレコード
ord-761c8943b06c4d2591ea631b3a32487e
出典データセット
uspto-grants-2000_02
特許番号
US06025375

関連ノート

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