[2,2'-Bithiophene]-5-carboxaldehyde → (5-Thiophen-2-ylthiophen-2-yl)methanol

HRID 1599507Notes

Reaction equation

HRID 1599507 reaction equation
[CH:1]([C:3]1[S:7][C:6]([C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)=[CH:5][CH:4]=1)=[O:2].[BH4-].[Na+]>CO>[OH:2][CH2:1][C:3]1[S:7][C:6]([C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 364428[2,2'-Bithiophene]-5-carboxaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 2776422(5-Thiophen-2-ylthiophen-2-yl)methanolYield 99.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-formyl-2,2'-bithiophene (20 g) in methanol (50 ml) was added sodium borohydride. The reaction mixture was stirred at room temperature and monitored with thin layer chromatography until the reaction completed. After removal of methanol, water was added to dissolve inorganic salts and extracted with dichloromethane. The extract was washed with brine, dried over anhydrous magnesium sulfate, concentrated to give product (20.1 g, 99%), melting point 52°-53° C.

Workup

  1. customAfter removal of methanol, water
  2. additionwas added
  3. dissolutionto dissolve inorganic salts
  4. extractionextracted with dichloromethane
  5. washThe extract was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-7f2bbbe184ee4db8b77cc5621eccf284
Source dataset
uspto-grants-1998_04
Patent number
US05741811

Reaction notes

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