Ethyl(6-chloro-1-benzofuran-3-yl)acetate → 2-(6-Chloro-1-benzofuran-3-yl)ethanol

HRID 1767993Notes

Reaction equation

HRID 1767993 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]([Cl:21])=[CH:20][C:15]=2[O:14][CH:13]=1)C>C1COCC1>[Cl: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 12936152Ethyl(6-chloro-1-benzofuran-3-yl)acetateHCID 21226445Aluminium lithium hydride

Product 1

HCID 236144432-(6-Chloro-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(6-chloro-1-benzofuran-3-yl)acetate (1.19 g, 50 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-chloro-1-benzofuran-3-yl)ethanol, was obtained as a white oil pure enough to be taken to the next step without purification. Yield: 900 mg (91%); 197 (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-367fc53f7ae34f33a09799f3355acc84
Source dataset
uspto-grants-2007_06
Patent number
US07235569B2

Reaction notes

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