Aluminium lithium hydride → 3-(2-Hydroxyethyl)-7-methoxybenzofuran

HRID 1768005

Reaction equation

HRID 1768005 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][CH:19]=[C:20]([O:21][CH3:22])[C:15]=2[O:14][CH:13]=1)C>C1COCC1>[CH3:22][O:21][C:20]1[C:15]2[O:14][CH:13]=[C:12]([CH2:11][CH2:10][OH:9])[C:16]=2[CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 22734085Ethyl(7-methoxy-1-benzofuran-3-yl)acetate

Product 1

HCID 226629353-(2-Hydroxyethyl)-7-methoxybenzofuran

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred suspension of LiAlH4 (200 mg, excess) in THF at 0° C., ethyl(7-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-(7-methoxy-1-benzofuran-3-yl)ethanol obtained as a white oil, was pure enough and taken to the next step without purification. Yield: 800 mg (83%); 193 (M+H).

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-d83110f8642d4bdfa4612a82f91eea31
Source dataset
uspto-grants-2007_06
Patent number
US07235569B2

Linked notes

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