2-Benzofurancarboxaldehyde → 1-Benzofuran-2-Ylmethanol

HRID 594314Notes

Reaction equation

HRID 594314 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-Ylmethanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A cooled (0° C.) solution of commercially available benzofuran-2-carbaldehyde (1.000 g; 6.84 mmol) in anh. methanol (37 ml) was treated portionwise with NaBH4 (1.294 g; 34.21 mmol), and the resulting mixture was stirred at 0° C., under nitrogen, for 1 h 45. After concentration to dryness under reduced pressure, the resulting residue was treated with water (30 ml), and extracted with DCM (2×100 ml). The mixed organic layers were washed with brine, dried over anh. MgSO4, filtered, concentrated to dryness under reduced pressure, and the residue was further dried under HV affording benzofuran-2-ylmethanol as a slightly yellow oil. LC-MS (conditions D): tR=0.78 min.; no ionisation.

Workup

  1. concentrationAfter concentration to dryness under reduced pressure
  2. additionthe resulting residue was treated with water (30 ml)
  3. extractionextracted with DCM (2×100 ml)
  4. washThe mixed organic layers were washed with brine
  5. dry with materialdried over anh. MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure
  8. customthe residue was further dried under HV

Sources & evidence

ORD record
ord-c049ebd00cbc414b9bef67fb5ad08dab
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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