1-Propanol → 2-Propoxythiophene

HRID 1464126Notes

Reaction equation

HRID 1464126 reaction equation
I[C:2]1[S:3][CH:4]=[CH:5][CH:6]=1.[Na].[CH2:8]([OH:11])[CH2:9][CH3:10]>>[CH2:8]([O:11][C:2]1[S:3][CH:4]=[CH:5][CH:6]=1)[CH2:9][CH3:10]

Participants

4

Reactant 3

HCID 10311-PropanolHCID 189212-IodothiopheneHCID 5360545Sodium

Product 1

HCID 190893322-PropoxythiopheneYield 13.5%

Procedure

Iodothiophene (59 g, 281 mmole) and cupric oxide (11.2 g, 141 mmole) were placed in propanol (420 g) containing sodium (19.7 g, 857 mmole). The mixture was stirred at reflux for 48 hours and then filtered. The filtrate was added to cold water and the water extracted with ethyl ether. The ether layers were combined, dried over magnesium sulfate, filtered, concentrated, and then vacuum distilled from over sodium at 50° C. and 10 torr to provide 5.4 g of product.

Workup

  1. temperatureat reflux for 48 hours
  2. filtrationfiltered
  3. additionThe filtrate was added to cold water
  4. extractionthe water extracted with ethyl ether
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. distillationvacuum distilled from over sodium at 50° C.

Sources & evidence

ORD record
ord-2a2513057be045588a9e1994a95d9d47
Source dataset
uspto-grants-1994_04
Patent number
US05302724

Reaction notes

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