Aluminium lithium hydride → HCID 18184294, compound

HRID 1768002Notes

Reaction equation

HRID 1768002 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]([F:21])[CH:19]=[CH:20][C:15]=2[O:14][CH:13]=1)C>C1COCC1>[F: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 21226445Aluminium lithium hydrideHCID 23614458Ethyl 2-(5-fluorobenzofuran-3-yl)acetate

Product 1

HCID 18184294HCID 18184294, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred suspension of LiAlH4 (200 mg, excess) in THF at 0° C., ethyl(5-fluoro-1-benzofuran-3-yl)acetate (1.11 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-(5-fluoro-1-benzofuran-3-yl)ethanol obtained as white oil and was pure enough to be taken to the next step without purification. Yield: 820 mg (91%); 181 (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-28733aec607f4a979f1ed69bacac7a5a
Source dataset
uspto-grants-2007_06
Patent number
US07235569B2

Reaction notes

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