Water → HCID 68193215, compound

HRID 1626791Notes

Reaction equation

HRID 1626791 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([CH3:21])([CH3:20])[C:15](OCC)=[O:16])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([CH3:21])([CH3:20])[CH2:15][OH:16])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 68193186HCID 68193186, compound

Product 1

HCID 68193215HCID 68193215, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 2-(4′-bromobiphenyl-4-yl)-2-methylpropionate (6.2 g, 18 mmol) was dissolved in tetrahydrofuran (150 mL), and lithium aluminum hydride (0.68 g, 18 mmol) was added at 0° C., followed by stirring at the same temperature for 1.5 hours. Water was added to the reaction solution, and the insolubles were filtered with celite, followed by extraction with ethyl acetate. After the solvent was distilled off under reduced pressure, the resulting residue was purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: hexane/ethyl acetate), and a fraction corresponding to the Rf value=0.40 (hexane/ethyl acetate=1/1) by thin layer chromatography was concentrated under reduced pressure to afford the title compound (5.0 g, 16 mmol) as a white solid (yield 92%).

Workup

  1. filtrationthe insolubles were filtered with celite
  2. extractionfollowed by extraction with ethyl acetate
  3. distillationAfter the solvent was distilled off under reduced pressure
  4. customthe resulting residue was purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: hexane/ethyl acetate)
  5. concentrationa fraction corresponding to the Rf value=0.40 (hexane/ethyl acetate=1/1) by thin layer chromatography was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ac47149840164ad68e83ff0729b2c7e8
Source dataset
uspto-grants-2014_07
Patent number
US08785462B2

Reaction notes

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