Ethylene Glycol → 2-(Thiophen-3-yloxy)-ethanol

HRID 641831

Reaction equation

HRID 641831 reaction equation
I[C:2]1[CH:6]=[CH:5][S:4][CH:3]=1.[H-].[Li+].[CH2:9]([OH:12])[CH2:10][OH:11]>[Cu].S([O-])([O-])(=O)=O.[Cu+2]>[S:4]1[CH:5]=[CH:6][C:2]([O:11][CH2:10][CH2:9][OH:12])=[CH:3]1

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 62714Lithium hydrideHCID 663323-Iodothiophene

Product 1

HCID 220362782-(Thiophen-3-yloxy)-ethanol

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 24462Copper SulfateCatalyst

Conditions

Temperature
100 °C

Procedure

To a solution of 1.0 g (4.76 mmol) 3-iodothiophene in 5 ml ethylene glycol is added 109 mg (1.71 mmol) copper powder, 114 mg (0.714 mmol) copper(II)sulphate and 151 mg (19.0 mmol) lithium hydride. The reaction mixture is heated overnight in a sealed flask at 100° C. The reaction mixture is filtered through Celite and evaporated. The resulting oil is then filtered through a 50 g silica pad and eluted with ethyl acetate/hexanes (7:3) to give after evaporation 750 mg of an orange liquid, which is used without purification directly in the next reaction.

Workup

  1. filtrationThe reaction mixture is filtered through Celite
  2. customevaporated
  3. filtrationThe resulting oil is then filtered through a 50 g silica pad
  4. washeluted with ethyl acetate/hexanes (7:3)
  5. customto give
  6. customafter evaporation 750 mg of an orange liquid, which
  7. customis used without purification directly in the next reaction

Sources & evidence

ORD record
ord-b72021451879433ca950fd89b43b8f12
Source dataset
uspto-grants-2010_04
Patent number
US07696216B2

Linked notes

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