2-Methoxythiophene → HCID 19004463, compound

HRID 2225623Notes

Reaction equation

HRID 2225623 reaction equation
[CH3:1][O:2][C:3]1[S:4][CH:5]=[CH:6][CH:7]=1.[CH:8]1([O:16][CH2:17]CO)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1>C1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH:8]1([O:16][CH2:17][CH2:1][O:2][C:3]2[S:4][CH:5]=[CH:6][CH:7]=2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

5

Reactant 2

HCID 856102-MethoxythiopheneHCID 19004350HCID 19004350, compound

Product 1

HCID 19004463HCID 19004463, compoundYield 61.9%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 241BenzeneSolvent

Procedure

As in Example 1, a solution of 2-methoxythiophene (11.4 g) and 2-(cyclooctyloxy) ethanol (13.78 g) in benzene (200 mL) containing para-toluenesulfonic acid (0.1 g) was stirred at reflux for 3 days in a flask equipped with a Soxhlet extractor charged with 4 Å molecular sieves. After the reaction was worked up in the usual manner, the crude product was purified by HPLC (hexane-diethyl ether; 2.4: 1) to give 12.6 g of 2-[[2-(cyclooctyloxy) ethyl]oxy]thiophene as a colorless oil. A small portion was distilled in a Kugelrohr apparatus (~130 ° C./0.02 mm) to furnish the analytical specimen.

Workup

  1. temperatureat reflux for 3 days in a flask
  2. customequipped with a Soxhlet extractor
  3. additioncharged with 4 Å molecular sieves
  4. customthe crude product was purified by HPLC (hexane-diethyl ether; 2.4: 1)

Sources & evidence

ORD record
ord-b1afdb67681942ee8779df940f10cb10
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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