Aluminium lithium hydride → (4-(Benzofuran-2-ylmethoxy)phenyl)methanol

HRID 2061382Notes

Reaction equation

HRID 2061382 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[CH2:10][O:11][C:12]1[CH:22]=[CH:21][C:15]([C:16](OCC)=[O:17])=[CH:14][CH:13]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[CH2:10][O:11][C:12]1[CH:22]=[CH:21][C:15]([CH2:16][OH:17])=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 59603176Ethyl 4-(benzofuran-2-ylmethoxy)benzoate

Product 1

HCID 66601277(4-(Benzofuran-2-ylmethoxy)phenyl)methanolYield 58.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound 93 (300 mg, 1.01 mmol) was dissolved in THF (15 mL) and LiAlH4 (38 mg, 1.01 mmol) was added portionwise, with vigorous stirring. The suspension was stirred at room temperature for 1 h. THF was evaporated off in-vacuo. The crude residue was taken up in EtOAc and washed with water, brine and dried (MgSO4). EtOAc was evaporated off in-vacuo to obtain (4-(benzofuran-2-ylmethoxy)phenyl)methanol (150 mg, 0.59 mmol), as a crude product. This was used in the next step without further purification.

Workup

  1. customTHF was evaporated off in-vacuo
  2. washwashed with water, brine
  3. dry with materialdried (MgSO4)
  4. customEtOAc was evaporated off in-vacuo

Sources & evidence

ORD record
ord-f6963dc7b87748f1ad0cebd407f32770
Source dataset
uspto-grants-2012_10
Patent number
US08283340B2

Reaction notes

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