Ammonium Chloride → 1-(6-Methoxy-benzofuran-3-yl)-ethane-1,2-diol

HRID 273335Notes

Reaction equation

HRID 273335 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][O:8][C:9]1[CH:23]=[CH:22][C:12]2[C:13]([C:16](=[O:21])[C:17](OC)=[O:18])=[CH:14][O:15][C:11]=2[CH:10]=1.[NH4+].[Cl-]>C1COCC1>[CH3:7][O:8][C:9]1[CH:23]=[CH:22][C:12]2[C:13]([CH:16]([OH:21])[CH2:17][OH:18])=[CH:14][O:15][C:11]=2[CH:10]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 69194602Methyl 2-(6-methoxybenzofuran-3-yl)-2-oxoacetate

Product 1

HCID 691973081-(6-Methoxy-benzofuran-3-yl)-ethane-1,2-diol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

LAH (0.093 g, 2.39 mmol) was added to a mixture of methyl 2-(6-methoxybenzofuran-3-yl)-2-oxoacetate (0.280 g, 1.196 mmol) in THF (10 mL) at 0° C. under N2, and the mixture was stirred overnight at room temperature under N2. An aqueous NH4Cl solution (5 mL) was added, and the reaction mixture was concentrated to half its volume and extracted with EtOAc. The organic layer was washed with brine and water, dried over anhydrous MgSO4, and evaporated to give 1-(6-methoxy-benzofuran-3-yl)-ethane-1,2-diol.

Workup

  1. concentrationthe reaction mixture was concentrated to half its volume
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine and water
  4. dry with materialdried over anhydrous MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-407fc36caef04f27a9e0c8ae1aef4275
Source dataset
uspto-grants-2008_11
Patent number
US07456289B2

Reaction notes

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