Ethyl(5-methoxy-1-benzofuran-3-yl)acetate → 2-(5-Methoxy-1-benzofuran-3-yl)ethanol

HRID 1768009Notes

Reaction equation

HRID 1768009 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C([O:9][C:10](=O)[CH2:11][C:12]1[C:16]2[CH:17]=[C:18]([O:21][CH3:22])[CH:19]=[CH:20][C:15]=2[O:14][CH:13]=1)C>C1COCC1>[CH3:22][O:21][C:18]1[CH:19]=[CH:20][C:15]2[O:14][CH:13]=[C:12]([CH2:11][CH2:10][OH:9])[C:16]=2[CH:17]=1

Participants

4

Reactant 2

HCID 15618718Ethyl(5-methoxy-1-benzofuran-3-yl)acetateHCID 21226445Aluminium lithium hydride

Product 1

HCID 149828732-(5-Methoxy-1-benzofuran-3-yl)ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred suspension of LiAlH4 (200 mg, excess) in THF at 0° C., ethyl(5-methoxy-1-benzofuran-3-yl)acetate (1.17 g, 5 mmol) in THF (20 mL) was added slowly. After the addition, reaction mixture was stirred at room temperature for 1 hr and quenched with saturated NH4Cl solution. The product was extracted with chloroform and washed well with water. It was dried over anhydrous MgSO4; filtered and concentrated. The product, 2-(5-methoxy-1-benzofuran-3-yl)ethanol, obtained as white oil, was pure enough and taken to the next step without purification. Yellow oil; Yield: 900 mg (93%); 193 (M+H).

Workup

  1. additionAfter the addition, reaction mixture
  2. customquenched with saturated NH4Cl solution
  3. extractionThe product was extracted with chloroform
  4. washwashed well with water
  5. dry with materialIt was dried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b4a784503a2740d3a155502c3f9267f2
Source dataset
uspto-grants-2007_06
Patent number
US07235569B2

Reaction notes

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