Water → 4,4-Dimethyl-2-(4'hydroxymethylbiphenyl-2-yl)oxazoline

HRID 1080903Notes

Reaction equation

HRID 1080903 reaction equation
[CH3:1][C:2]1([CH3:23])[CH2:6][O:5][C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:13]2[CH:18]=[CH:17][C:16]([C:19](OC)=[O:20])=[CH:15][CH:14]=2)=[N:3]1.[H-].[Li+].[Al+3].[H-].[H-].[H-].O>O1CCCC1>[CH3:1][C:2]1([CH3:23])[CH2:6][O:5][C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:13]2[CH:14]=[CH:15][C:16]([CH2:19][OH:20])=[CH:17][CH:18]=2)=[N:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 153808774,4-Dimethyl-2-(4'-methoxycarbonylbiphenyl-2-yl)oxazolineHCID 21226445Aluminium lithium hydride

Product 1

HCID 110658764,4-Dimethyl-2-(4'hydroxymethylbiphenyl-2-yl)oxazolineYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.0 g (6.46 mmol) of 4,4-dimethyl-2-(4'-methoxycarbonylbiphenyl-2-yl)oxazoline was dissolved in tetrahydrofuran (20 ml). 0.49 g (12.9 mmol) of aluminum lithium hydride was gradually added thereto under cooling with ice, followed by the stirring for 2 hours as such. Water (50 ml) was added thereto to conduct hydrolysis, followed by the extraction with chloroform. After washing with water and drying, vacuum concentration was conducted. The residue was purified by silica gel column chromatography (a n-hexane/ethyl acetate system) to give 1.69 g of the title compound (yield 93%).

Workup

  1. temperatureunder cooling with ice
  2. customstirring for 2 hours
  3. customhydrolysis
  4. extractionfollowed by the extraction with chloroform
  5. washAfter washing with water
  6. customdrying
  7. concentrationvacuum concentration
  8. customThe residue was purified by silica gel column chromatography (a n-hexane/ethyl acetate system)

Sources & evidence

ORD record
ord-749ccf234f1d43c7977014a0e4f33dce
Source dataset
uspto-grants-1996_12
Patent number
US05583229

Reaction notes

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