2-(4-Hydroxyphenyl)-3-[4-[2-(piperidin-1-yl)ethoxy]benzoyl]-6-hydroxybenzofuran → [2-(4-Hydroxyphenyl)-6-hydroxybenzofuran-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methanol

HRID 48253Notes

Reaction equation

HRID 48253 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:33]=[C:32]([OH:34])[CH:31]=[CH:30][C:11]=3[C:12]=2[C:13]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][N:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)=[CH:17][CH:16]=2)=[O:14])=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:33]=[C:32]([OH:34])[CH:31]=[CH:30][C:11]=3[C:12]=2[CH:13]([C:15]2[CH:16]=[CH:17][C:18]([O:21][CH2:22][CH2:23][N:24]3[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]3)=[CH:19][CH:20]=2)[OH:14])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 99557562-(4-Hydroxyphenyl)-3-[4-[2-(piperidin-1-yl)ethoxy]benzoyl]-6-hydroxybenzofuranHCID 21226445Aluminium lithium hydride

Product 1

HCID 12968229[2-(4-Hydroxyphenyl)-6-hydroxybenzofuran-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methanolYield 57.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4.57 g (0.01 mol) of [2-(4-hydroxyphenyl)-6-hydroxybenzofuran-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl] methanone was dissolved in 250 mL of THF and 2 g (0.053 mol) of LiAlH4 was slowly added over a period of twenty minutes to the stirring solution. The reaction mixture was stirred and kept under a nitrogen atmosphere and the reaction was allowed to proceed for eighteen hours at room temperature and then it was concentrated to dryness in vacuo. 500 mL of EtOAc was slowly added along with 2 mL of water. After stirring for 10 minutes, 500 mL of water was added and the EtOAc layer was removed. The EtOAc layer was washed with an additional 500 mL of water and the layers were separated. The EtOAc layer was dried with anhydrous Na2SO4 and concentrated to dryness to yield 2.66 g of the title compound as tan amorphous powder.

Workup

  1. waitto proceed for eighteen hours at room temperature
  2. concentrationit was concentrated to dryness in vacuo
  3. addition500 mL of EtOAc was slowly added along with 2 mL of water
  4. stirringAfter stirring for 10 minutes
  5. addition500 mL of water was added
  6. customthe EtOAc layer was removed
  7. washThe EtOAc layer was washed with an additional 500 mL of water
  8. customthe layers were separated
  9. dry with materialThe EtOAc layer was dried with anhydrous Na2SO4
  10. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-0d28696821f74aee8587ed8722bf4a8d
Source dataset
uspto-grants-2004_03
Patent number
US06703407B1

Reaction notes

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