Aluminium lithium hydride → HCID 23614446, compound

HRID 1768028Notes

Reaction equation

HRID 1768028 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([C:9]([C:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[C:22]([O:23][CH3:24])[C:17]=2[O:16][CH:15]=1)(C)[C:10]([O-])=[O:11])C>C1COCC1>[CH3:24][O:23][C:22]1[C:17]2[O:16][CH:15]=[C:14]([CH:9]([CH3:7])[CH2:10][OH:11])[C:18]=2[CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86595775HCID 86595775, compound

Product 1

HCID 23614446HCID 23614446, compound

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)propanoate (1.24 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)-1-propanol, was obtained as white oil, was pure enough and taken to the next step without purification. Yield: 900 mg (87%); 207 (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-b21d955aedb446af81f3e5d1a68fadd4
Source dataset
uspto-grants-2007_06
Patent number
US07235569B2

Reaction notes

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