Water → HCID 67119374, compound

HRID 2076691Notes

Reaction equation

HRID 2076691 reaction equation
[CH2:1]([C:3]1[C:8]([C:9](OC)=[O:10])=[CH:7][CH:6]=[CH:5][C:4]=1[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1)[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH2:1]([C:3]1[C:8]([CH2:9][OH:10])=[CH:7][CH:6]=[CH:5][C:4]=1[C:13]1[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=1)[CH3:2]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 67119103HCID 67119103, compound

Product 1

HCID 67119374HCID 67119374, compoundYield 101.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

After methyl 2-ethyl-4′-methoxy-1,1′-biphenyl-3-carboxylate (4.83 g, 17.9 mmol) obtained in Example (90-2) was added to a suspension of lithium aluminum hydride (1.02 g, 26.8 mmol) in tetrahydrofuran (90 ml) under ice-cooling, the mixture was stirred at room temperature for 30 minutes. The reaction mixture was cooled with ice and water (1 ml) was added dropwise thereto. After the mixture was stirred for 5 minutes, a 3N aqueous sodium hydroxide solution (1 ml) was added thereto at room temperature and the mixture was stirred for 5 minutes. Further, water (3 ml) was added thereto and the mixture was stirred for 20 minutes. After the insolubles were removed by filtration using Celite, the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=4/1-3/1) to give (2-ethyl-4′-methoxy-1,1′-biphenyl-3-yl)methanol (4.39 g, yield: 100%).

Workup

  1. temperaturecooling
  2. additionwas added dropwise
  3. stirringAfter the mixture was stirred for 5 minutes
  4. stirringat room temperature and the mixture was stirred for 5 minutes
  5. stirringthe mixture was stirred for 20 minutes
  6. customAfter the insolubles were removed by filtration
  7. customthe solvent was removed under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=4/1-3/1)

Sources & evidence

ORD record
ord-6ff5c5e44bcb4946b73e889d20d0c049
Source dataset
uspto-grants-2011_04
Patent number
US07923573B2

Reaction notes

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