Benzofuran-2-carboxylic acid → 1-Benzofuran-2-Ylmethanol

HRID 1030266Notes

Reaction equation

HRID 1030266 reaction equation
B#B.[O:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH:5]=[C:4]1[C:12](O)=[O:13]>O1CCCC1>[O:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH:5]=[C:4]1[CH2:12][OH:13]

Participants

4

Reactant 2

HCID 10331Benzofuran-2-carboxylic acidHCID 6328200Diboron

Product 1

HCID 27762631-Benzofuran-2-YlmethanolYield 78.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1 Molar diborane in tetrahydrofuran (61.6 mL, 61.6 mmol) was added dropwise over 10 minutes to a stirred solution of benzofuran-2-carboxylic acid (5.00 g, 30.8 mmol) in tetrahydrofuran (50 mL) at 0° C. Stirring was continued at 0° C. for 30 minutes, then at room temperature for 18 hours. The reaction mixture was quenched carefully by slow addition of 1:1 THF/H2O, and extracted with ether. The organic extracts were dried (MgSO4) and concentrated to afford 3.58 g (78%) of product as a colorless oil.

Workup

  1. waitat room temperature for 18 hours
  2. customThe reaction mixture was quenched carefully by slow addition of 1:1 THF/H2O
  3. extractionextracted with ether
  4. dry with materialThe organic extracts were dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-bafb03749d234d408fe0f661c739b440
Source dataset
uspto-grants-1992_04
Patent number
US05104892

Reaction notes

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