Sodium cyanoborohydride → HCID 68707780, compound

HRID 29423Notes

Reaction equation

HRID 29423 reaction equation
[C:1]([O:5][C:6]([C:8]1[O:9][C:10]2[CH:17]=[CH:16][C:15]([CH:18]=O)=[C:14]([OH:20])[C:11]=2[C:12]=1[CH3:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([BH3-])#N.[Na+]>C1COCC1>[C:1]([O:5][C:6]([C:8]1[O:9][C:10]2[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([OH:20])[C:11]=2[C:12]=1[CH3:13])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 865990315-Formyl-4-hydroxy-3-methyl-benzofuran-2-carboxylic acid tert-butyl ester

Product 1

HCID 68707780HCID 68707780, compoundYield 17.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 5-formyl-4-hydroxy-3-methyl-benzofuran-2-carboxylic acid tert-butyl ester (430 mg, 1.56 mmol) was added 8 mL of THF, and sodium cyanoborohydride (117 mg, 1.87 mmol) was added in one portion. The solution was stirred at room temperature for 1 h and then placed in a 65° C. oil bath overnight. The solvent was removed under vacuum and water was added. The mixture was extracted with ethyl acetate. Removal of the solvent gave the crude product, which was purified by column chromatography to give 70 mg of 4-hydroxy-3,5-dimethyl-benzofuran-2-carboxylic acid tert-butyl ester as a white solid.

Workup

  1. additionwas added in one portion
  2. customplaced in a 65° C.
  3. customovernight
  4. customThe solvent was removed under vacuum and water
  5. additionwas added
  6. extractionThe mixture was extracted with ethyl acetate
  7. customRemoval of the solvent
  8. customgave the crude product, which
  9. customwas purified by column chromatography

Sources & evidence

ORD record
ord-3ccab5dda0064efeb0c9488a3a493164
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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