Methyl benzofuran-7-carboxylate → Benzofuran-7-ylmethanol

HRID 1602443Notes

Reaction equation

HRID 1602443 reaction equation
[O:1]1[C:5]2[C:6]([C:10](OC)=[O:11])=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[CH:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[O:1]1[C:5]2[C:6]([CH2:10][OH:11])=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[CH:2]1

Participants

4

Reactant 2

HCID 14229730Methyl benzofuran-7-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 18787422Benzofuran-7-ylmethanolYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl benzofuran-7-carboxylate (5.34 g, 30 mmol) was added to a suspension of LAH (2.31 g, 61 mmol) in THF and then heated to reflux for 30 min. The reaction was quenched with ethyl acetate and water. The mixture was made acidic with 12N HCl until all the precipitate dissolved. The ethyl acetate layer was separated, washed with water, dried with brine, and concentrated in vacuo to give a yellow oil (4.03 g, 91%).

Workup

  1. temperatureheated
  2. temperatureto reflux for 30 min
  3. customThe reaction was quenched with ethyl acetate and water
  4. dissolutiondissolved
  5. customThe ethyl acetate layer was separated
  6. washwashed with water
  7. dry with materialdried with brine
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c1ff4e68e9c840dabb6e9364425ef5d7
Source dataset
uspto-grants-1999_11
Patent number
US05981571

Reaction notes

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