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

HRID 12022

반응식

HRID 12022 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

HCID 686809722-Tert-butyl-6-chlorocyclohexanone수율 81%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

반응 조건

온도
-78 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-2490bc6217a344258faf2fe00e97dd10
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07727979B2

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