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

HRID 2259208Notes

Reaction equation

HRID 2259208 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-fad93f897b9a418cb12d655d36b2c33f
Source dataset
uspto-grants-1995_12
Patent number
US05472962

Reaction notes

Loading…