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

HRID 1289120Notes

Reaction equation

HRID 1289120 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)methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

20 g of 5-formyl-2,2'-bithiophene was dissolved in 50 ml of methanol, followed by adding NaBH4 and stirring until bubbling stopped. The reaction was monitored by thin layer chromatography to determine whether the reaction was completed. After the methanol was removed under reduced pressure and the reaction solution was extracted with dichloromethane, the solution was washed with saturated NaCl solution, dried over anhydrous magnesium sulfate, condensed and 20.10 g of product (melting point 52°-53° C., 99%) was thus obtained.

Workup

  1. customuntil bubbling
  2. customAfter the methanol was removed under reduced pressure
  3. extractionthe reaction solution was extracted with dichloromethane
  4. washthe solution was washed with saturated NaCl solution
  5. dry with materialdried over anhydrous magnesium sulfate, condensed and 20.10 g of product (melting point 52°-53° C., 99%)
  6. customwas thus obtained

Sources & evidence

ORD record
ord-0722be866f9743478aa58e297577f94c
Source dataset
uspto-grants-1998_05
Patent number
US05747525

Reaction notes

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