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

HRID 635528Notes

Reaction equation

HRID 635528 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10](O)=[O:11].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1.C(OCC)C>[OH:11][CH2:10][C:2]1[O:1][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 10331Benzofuran-2-carboxylic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 27762631-Benzofuran-2-YlmethanolYield 49%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of benzofuran 2-carboxylic acid (2.50 g) in tetrahydrofuran (50 ml) at 0° C. under nitrogen was added a solution of lithium aluminium hydride (1.0M; 7.7 ml) in tetrahydrofuran. Stirring was continued for 2 h, allowing the temperature to rise to RT. The mixture was diluted with diethyl ether (50 ml) and quenched with water (30 ml). The aqueous layer was separated and extracted with diethyl ether (2×25 ml). The combined extracts were washed with water (30 ml), sodium hydroxide solution (1M; 30 ml), water (30 ml), brine (30 ml) and dried (MgSO4). Filtration and evaporation of solvent under reduced pressure yielded the title compound (1.11 g, 49%) as a colourless oil.

Workup

  1. customto rise to RT
  2. customquenched with water (30 ml)
  3. customThe aqueous layer was separated
  4. extractionextracted with diethyl ether (2×25 ml)
  5. washThe combined extracts were washed with water (30 ml), sodium hydroxide solution (1M; 30 ml), water (30 ml), brine (30 ml)
  6. dry with materialdried (MgSO4)
  7. filtrationFiltration and evaporation of solvent under reduced pressure

Sources & evidence

ORD record
ord-0074004be21c4672bd51ee6045a00c17
Source dataset
uspto-grants-2001_02
Patent number
US06187924B1

Reaction notes

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