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

HRID 2259208

Reaktionsgleichung

Reaktionsgleichung von HRID 2259208
[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

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-fad93f897b9a418cb12d655d36b2c33f
Quelldatensatz
uspto-grants-1995_12
Patentnummer
US05472962

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