Ethyl(5-chloro-1-benzofuran-3-yl)acetate → 2-(5-Chloro-1-benzofuran-3-yl)ethanol

HRID 1767999Notes

Reaction equation

HRID 1767999 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]([Cl:21])[CH:19]=[CH:20][C:15]=2[O:14][CH:13]=1)C>C1COCC1>[Cl: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 12936153Ethyl(5-chloro-1-benzofuran-3-yl)acetateHCID 21226445Aluminium lithium hydride

Product 1

HCID 236144382-(5-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(5-chloro-1-benzofuran-3-yl)acetate (1.19 g, 50 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-chloro-1-benzofuran-3-yl)ethanol, was obtained as a white oil pure enough to be taken to the next step without purification. Yield: 850 mg (86%); 197 (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-56ce5de6d94443a6b9939efe9a4d9c95
Source dataset
uspto-grants-2007_06
Patent number
US07235569B2

Reaction notes

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