Potassium Carbonate → 6-Methoxy-1-benzothiophene

HRID 1825056Notes

Reaction equation

HRID 1825056 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([SH:9])[CH:6]=[CH:7][CH:8]=1.C([O-])([O-])=O.[K+].[K+].[CH2:16](OC(OCC)CBr)[CH3:17]>CC(C)=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]2[CH:17]=[CH:16][S:9][C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 849893-Methoxybenzenethiol

Product 1

HCID 136342376-Methoxy-1-benzothiopheneYield 155.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 3-methoxybenzenethiol (10 ml, 11.30 g, 80 mmole), K2CO3 (11.15 g, 80 mmole) and bromoacetaldehyde diethyl acetal (12 ml, 15.72 g, 80 mmole) in acetone (100 ml) was stirred at ambient temperature for 16 hours, then filtered. The filtrate was subsequently concentrated, in vacuo. The residue obtained was partitioned between H2O (150 ml) and Et2O (150 ml). The layers were separated and the aqueous phase was extracted with Et2O (150 ml). The combined organic extracts were washed with 0.5 M KOH (aq), H2O and brine, then dried over Na2SO4 and concentrated, in vacuo, to give 20.4 g of an amber oil which was used directly in the subsequent cyclization without any further purification.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was subsequently concentrated, in vacuo
  3. customThe residue obtained
  4. customwas partitioned between H2O (150 ml) and Et2O (150 ml)
  5. customThe layers were separated
  6. extractionthe aqueous phase was extracted with Et2O (150 ml)
  7. washThe combined organic extracts were washed with 0.5 M KOH (aq), H2O and brine
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated, in vacuo

Sources & evidence

ORD record
ord-227152e424f542fc86e8e40016326011
Source dataset
uspto-grants-2006_05
Patent number
US07045528B2

Reaction notes

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