5-Formylthiophene-3-carboxylic acid → 5-(Hydroxymethyl)thiophene-3-carboxylic acid

HRID 900990Notes

Reaction equation

HRID 900990 reaction equation
[BH4-].[Na+].[CH:3]([C:5]1[S:9][CH:8]=[C:7]([C:10]([OH:12])=[O:11])[CH:6]=1)=[O:4]>O.C(O)C>[OH:4][CH2:3][C:5]1[S:9][CH:8]=[C:7]([C:10]([OH:12])=[O:11])[CH:6]=1

Participants

5

Reactant 2

HCID 8188835-Formylthiophene-3-carboxylic acidHCID 4311764Sodium borohydride

Product 1

HCID 596988145-(Hydroxymethyl)thiophene-3-carboxylic acidYield 70%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A solution of sodium borohydride (12.5 g, 330 mmol) in water (150 mL) and ethanol (100 mL) at 0° C. is charged with 5-formyl-thiophene-3-carboxylic acid (20.6 g, 132 mmol) in one portion. After warming to room temperature and stirring for 4 h, the mixture is diluted with water and the resulting precipitate vacuum filtered. The filtrate is concentrated and the resulting aqueous solution is washed with ether (2×). The aq layer is acidified with concentrated HCl and extracted with ether (3×). The combined ether extracts are dried over Na2SO4, filtered and concentrated in vacuo to give 5-hydroxymethyl-thiophene-3-carboxylic acid (14.6, 70%) as a white solid; mp 149° C.; 1H NMR (DMSO-d6, 300 MHz) δ 12.60 (s, 1 H), 8.10 (s, 1 H), 7.20 (s, 1 H), 5.52 (t, J=6.0 Hz, 1 H), 4.60 (s, 2 H).

Workup

  1. filtrationthe resulting precipitate vacuum filtered
  2. concentrationThe filtrate is concentrated
  3. washthe resulting aqueous solution is washed with ether (2×)
  4. extractionextracted with ether (3×)
  5. dry with materialThe combined ether extracts are dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c3d37f22fed6431ca0d54f9768456c11
Source dataset
uspto-grants-2008_04
Patent number
US07361671B2

Reaction notes

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