4-Toluenesulfonyl chloride → 2-Tert-butyl-6-chlorocyclohexanone

HRID 12022

反応式

HRID 12022 の反応式
C(NC(C)C)(C)C.[C:8]([CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][C:13]1=[O:18])([CH3:11])([CH3:10])[CH3:9].C1(C)C=CC(S([Cl:28])(=O)=O)=CC=1>O1CCCC1>[C:8]([CH:12]1[CH2:17][CH2:16][CH2:15][CH:14]([Cl:28])[C:13]1=[O:18])([CH3:11])([CH3:9])[CH3:10]

参加物

5

反応物 3

HCID 73974-Toluenesulfonyl chlorideHCID 7912DiisopropylamineHCID 1026812-tert-Butylcyclohexanone

生成物 1

HCID 686809722-Tert-butyl-6-chlorocyclohexanone収率 81%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
-78 °C

実験手順

N-butyl lithium is added dropwise to a solution, cooled to 0° C., of diisopropylamine (5.5 mmol) in dry tetrahydrofuran. After the addition is complete the mixture is cooled to −78° C., and a solution of 2-tert-butylcyclohexanone (5 mmol) in dry tetrahydrofuran (50 ml) is introduced, followed by the addition of p-toluenesulphonyl chloride (5 mmol), also dissolved in dry tetrahydrofuran (50 ml). The reaction mixture is heated to room temperature and after stirring for 30 mins over silica gel filtered with ether as eluant. After concentration by evaporation in a vacuum 2-tert-butyl-6-chlorcyclohexanone (760 mg) is obtained in a yield of 81% (Tet. Lett. 1999, 40(12), 2231-2234).

後処理

  1. additionAfter the addition
  2. temperatureThe reaction mixture is heated to room temperature
  3. filtrationfiltered with ether as eluant
  4. concentrationAfter concentration
  5. customby evaporation in a vacuum 2-tert-butyl-6-chlorcyclohexanone (760 mg)
  6. customis obtained in a yield of 81% (Tet. Lett. 1999, 40(12), 2231-2234)

出典と根拠

ORDレコード
ord-2490bc6217a344258faf2fe00e97dd10
出典データセット
uspto-grants-2010_06
特許番号
US07727979B2

関連ノート

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