Cyclohexanone → 2-(1-Hydroxycyclohexyl)-6-methoxybenzothiophene

HRID 2259208

반응식

HRID 2259208 반응식
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH:10]=[CH:9][S:8][C:7]=2[CH:11]=1.C([Li])CCC.[C:17]1(=[O:23])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.[Cl-].[NH4+]>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH:10]=[C:9]([C:17]3([OH:23])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)[S:8][C:7]=2[CH:11]=1

참가 물질

6

반응물 4

HCID 7967CyclohexanoneHCID 25517Ammonium ChlorideHCID 136342376-Methoxy-1-benzothiopheneHCID 178418339Butyllithium

생성물 1

HCID 190027692-(1-Hydroxycyclohexyl)-6-methoxybenzothiophene

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

3.2 g of 6-methoxybenzo[b]thiophene was dissolved in 3 ml of THF and the solution was cooled with ice. 18.6 ml of n-butyllithium (15% hexane solution) was gradually added in a stream of nitrogen and the mixture was stirred. A THF solution of 3.1 ml of cyclohexanone was added and the mixture was stirred at room temperature for 6 hours. 35 ml of saturated aqueous ammonium chloride solution was added to the reaction mixture, the resultant mixture was extracted with ether, and the extract was dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resultant crude product was purified by TLC (developing solvent, chloroform) to obtain 2.8 g of 6-methoxy-2-(1-hydroxycyclohexyl)benzo[b]thiophene.

후처리

  1. temperaturethe solution was cooled with ice
  2. stirringthe mixture was stirred at room temperature for 6 hours
  3. extractionthe resultant mixture was extracted with ether
  4. dry with materialthe extract was dried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off
  6. customthe resultant crude product was purified by TLC (developing solvent, chloroform)

출처 및 근거

ORD 기록
ord-fad93f897b9a418cb12d655d36b2c33f
출처 데이터셋
uspto-grants-1995_12
특허 번호
US05472962

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