Sodium borohydride → 2-Hydroxymethyl-5-(3,4,5-trimethoxyphenyl)thiophene

HRID 993036Notes

Reaction equation

HRID 993036 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[S:17][C:16]([CH:18]=[O:19])=[CH:15][CH:14]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[BH4-].[Na+]>CO>[OH:19][CH2:18][C:16]1[S:17][C:13]([C:5]2[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 184084975-(3,4,5-Trimethoxyphenyl)thiophene-2-carboaldehyde

Product 1

HCID 184084922-Hydroxymethyl-5-(3,4,5-trimethoxyphenyl)thiophene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-(3,4,5-Trimethoxyphenyl)thiophene-2-carboaldehyde (662 mg) was dissolved in methanol (50 mL), and to the solution sodium borohydride (180 mg) was gradually added under ice cooling. After stirring the mixture at room temperature for 1 hour, the reaction mixture was concentrated under reduced pressure, and the residue was dissolved in chloroform. The resultant organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=3:1 to 2:1) to obtain the title compound.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in chloroform
  3. washThe resultant organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=3:1 to 2:1)

Sources & evidence

ORD record
ord-039b3983b489421ab45467e7dcdd430e
Source dataset
uspto-grants-2002_10
Patent number
US06472386B1

Reaction notes

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