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

HRID 1940937Notes

Reaction equation

HRID 1940937 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-9a941d485ffa48a68002f2f0350561f5
Source dataset
uspto-grants-1997_12
Patent number
US05700938

Reaction notes

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