Sodium borohydride → 7-Methoxy-3-hydroxy-2,2-dimethylbenzofuran

HRID 3772Notes

Reaction equation

HRID 3772 reaction equation
[BH4-].[Na+].[CH3:3][O:4][C:5]1[C:13]2[O:12][C:11]([CH3:15])([CH3:14])[C:10](=[O:16])[C:9]=2[CH:8]=[CH:7][CH:6]=1>C(O)C.C(Cl)Cl>[CH3:3][O:4][C:5]1[C:13]2[O:12][C:11]([CH3:14])([CH3:15])[CH:10]([OH:16])[C:9]=2[CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 141266477-Methoxy-2,2-dimethyl-3-benzofuranone

Product 1

HCID 141266487-Methoxy-3-hydroxy-2,2-dimethylbenzofuran

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

An aqueous solution of sodium borohydride (8.2 g, 50 ml) is added to a stirred solution of the product obtained in Step 3. (41.8 g) in ethanol (1 l) and the mixture refluxed for 3 hours and evaporated in vacuo. The residue is taken up in water and toluene, the layers are separated and the organic phase washed, dried and evaporated in vacuo affording an oil which is dissolved in methylene chloride, dried, filtered and evaporated in vacuo. The residue is dissolved in ethyl acetate and chromatographed on silica gel affording the desired product as a white solid.

Workup

  1. customevaporated in vacuo
  2. customtoluene, the layers are separated
  3. washthe organic phase washed
  4. customdried
  5. customevaporated in vacuo
  6. customaffording an oil which
  7. customdried
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. dissolutionThe residue is dissolved in ethyl acetate
  11. customchromatographed on silica gel affording the desired product as a white solid

Sources & evidence

ORD record
ord-5b26df7fe2534bf0910c119f65b7be7d
Source dataset
uspto-grants-1988_02
Patent number
US04722925

Reaction notes

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