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

HRID 342085Notes

Reaction equation

HRID 342085 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-ef5c89c266084ae6b4feaf6821bd683a
Source dataset
uspto-grants-1999_01
Patent number
US05856529

Reaction notes

Loading…