Water → 1-Benzofuran-2-Ylmethanol

HRID 709571Notes

Reaction equation

HRID 709571 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+].O>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

5

Reactant 3

HCID 962WaterHCID 613412-BenzofurancarboxaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 27762631-Benzofuran-2-YlmethanolYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Benzofurancarbaldehyde (2.2 g, 15 mmol) was dissolved in 25 mL of methanol. To this solution was added sodium borohydride (0.28 g, 7.5 mmol) in small portions over a period of 20 minutes. Then 2 mL of water were added and the mixture was evaporated. The residue was dissolved in ethyl acetate (75 mL) and washed with water (3×75 mL), dried (MgSO4) and evaporated, providing 2.1 g of benzofuran-2-yl-methanol, in 95% yield; 1H NMR (CDCl3) δ 2.03 (t, J=6.1 Hz, 1H), 4.77 (d, J=6.1 Hz, 214), 6.66 (s, 1H), 7.19-7.32 (m, 2H), 7.45-7.50 (m, 1H), 7.53-7.57 (m, 1H).

Workup

  1. customthe mixture was evaporated
  2. dissolutionThe residue was dissolved in ethyl acetate (75 mL)
  3. washwashed with water (3×75 mL)
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-172bb6bc91ab4511aff07602cb35129c
Source dataset
uspto-grants-2015_11
Patent number
US09181216B2

Reaction notes

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