2-Benzofurancarboxaldehyde → 1-Benzofuran-2-Ylmethanol

HRID 2071066Notes

Reaction equation

HRID 2071066 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[CH:10]=[O:11].[BH4-].[Na+]>CO>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[CH2:10][OH:11]

Participants

4

Reactant 2

HCID 613412-BenzofurancarboxaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 27762631-Benzofuran-2-YlmethanolYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirring solution of 1.02 g (6.96 mmol) of benzofuran-2-carbaldehyde (Aldrich) in 20 mL of MeOH at 0° C. was added 1.02 g (26.9 mmol) of NaBH4. The ice bath was removed, and the mixture was allowed to cool to r.t. (Reaction was exothermic). After 45 min., the mixture was concentrated, and H2O was added and 1N HCl to pH=7. The aqueous layer was extracted with EtOAc (2×), and the combined extracts were washed with brine, dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography provided 1 g of benzofuran-2-ylmethanol as a colorless oil in quantitative yield.

Workup

  1. customThe ice bath was removed
  2. custom(Reaction was exothermic)
  3. concentrationthe mixture was concentrated
  4. additionH2O was added
  5. extractionThe aqueous layer was extracted with EtOAc (2×)
  6. washthe combined extracts were washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification by flash silica gel chromatography

Sources & evidence

ORD record
ord-2399e049f09e4f4eb726413db44991be
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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