Aluminium lithium hydride → 2-(6-Methoxy-benzofuran-3-yl)ethanol

HRID 1178797Notes

Reaction equation

HRID 1178797 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]=[CH:18][C:19]([O:21][CH3:22])=[CH:20][C:15]=2[O:14][CH:13]=1)C>C1COCC1>[CH3:22][O:21][C:19]1[CH:18]=[CH:17][C:16]2[C:12]([CH2:11][CH2:10][OH:9])=[CH:13][O:14][C:15]=2[CH:20]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 23614459Ethyl(6-methoxy-1-benzofuran-3-yl)acetate

Product 1

HCID 236144442-(6-Methoxy-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(6-methoxy-1-benzofuran-3-yl)acetate (1.17 g, 5 mmol) in THF (20 mL) was added slowly. After the addition, the 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-(6-methoxy-1-benzofuran-3-yl)ethanol, was obtained as a white oil and was pure enough to be taken to the next step without purification. Yield: 850 mg (88%); (M+H): 193.

Workup

  1. additionAfter the addition
  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-bce9e73b7aa84f53a60a63bc5092de5c
Source dataset
uspto-grants-2007_10
Patent number
US07276603B2

Reaction notes

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