Sodium borohydride → 4,5 Dihydroxymethyl-2,2': 5',2"-terthiophene

HRID 1599514Notes

Reaction equation

HRID 1599514 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([C:10]2[S:11][C:12]([C:15]3[S:16][CH:17]=[CH:18][CH:19]=3)=[CH:13][CH:14]=2)[S:6][C:7]=1[CH2:8][OH:9])=[O:2].[BH4-].[Na+]>CO>[OH:2][CH2:1][C:3]1[CH:4]=[C:5]([C:10]2[S:11][C:12]([C:15]3[S:16][CH:17]=[CH:18][CH:19]=3)=[CH:13][CH:14]=2)[S:6][C:7]=1[CH2:8][OH:9]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 573213644-Formyl-5-hydroxymethyl-2,2':5', 2"-terthiophene

Product 1

HCID 539277724,5 Dihydroxymethyl-2,2': 5',2"-terthiopheneYield 99.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-formyl-5-hydroxymethyl-2,2':5', 2"-terthiophene (0.1 g) in methanol (10 ml) was added excess amount of sodium borohydride. The reaction mixture was stirred at room temperature for 40 minutes. Methanol was removed and water was added. The solution was extracted with ethyl acetate, washed with brine, dried over anhydrous magnesium sulfate and concentrated to give brownish solid product (0.1 g), melting point 99°-101° C.

Workup

  1. customMethanol was removed
  2. additionwater was added
  3. extractionThe solution was extracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f19eeda0b721487885aad9595c2afa01
Source dataset
uspto-grants-1998_04
Patent number
US05741811

Reaction notes

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