Aluminium lithium hydride → 6-(2,4-Difluoro-phenyl)-5-{hydroxy-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methyl}-naphthalen-2-ol

HRID 1513947Notes

Reaction equation

HRID 1513947 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([OH:19])[CH:15]=2)[C:10]=1[C:20]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][N:31]2[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]2)=[CH:24][CH:23]=1)=[O:21].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]([CH:20]([OH:21])[C:22]2[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][N:31]3[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]3)=[CH:24][CH:23]=2)=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14]([OH:19])[CH:13]=[CH:12]2

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 67004951[2-(2,4-Difluoro-phenyl)-6-hydroxy-naphthalen-1-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone

Product 1

HCID 670047256-(2,4-Difluoro-phenyl)-5-{hydroxy-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methyl}-naphthalen-2-olYield 102.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve [2-(2,4-difluoro-phenyl)-6-hydroxy-naphthalen-1-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone (3.3 g, 6.8 mmol) in dry THF (100 mL) and stir under nitrogen. Slowly add lithium aluminum hydride (0.9 g, 24 mmol) and heat to reflux. Cool to room temperature after 30 minutes and quench excess LiAlH4 with slow addition of ice. Dilute with water and adjust the pH to 7 with 1M HCl. Extract five times with 20% IPA in chloroform. Dry the combined organic layers with sodium sulfate, filter and concentrate in vacuo to yield 3.4 g (100%) of the title compound.

Workup

  1. customquench excess LiAlH4
  2. additionwith slow addition of ice
  3. additionDilute with water
  4. extractionExtract five times with 20% IPA in chloroform
  5. dry with materialDry the combined organic layers with sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-bf4394cc6f0f40d1a63dfdf56f2508f9
Source dataset
uspto-grants-2012_07
Patent number
US08217032B2

Reaction notes

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