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

HRID 53426Notes

Reaction equation

HRID 53426 reaction equation
[H-].[Li+].[Al+3].[H-].[H-].[H-].[CH3:7][C:8]1([CH3:28])[CH2:12][O:11][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]2[CH:24]=[CH:23][C:22]([C:25](O)=[O:26])=[CH:21][CH:20]=2)=[N:9]1.O>O1CCCC1>[CH3:7][C:8]1([CH3:28])[CH2:12][O:11][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]2[CH:20]=[CH:21][C:22]([CH2:25][OH:26])=[CH:23][CH:24]=2)=[N:9]1

Participants

5

Reactant 3

HCID 962WaterHCID 15289161HCID 15289161, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 110658764,4-Dimethyl-2-(4'hydroxymethylbiphenyl-2-yl)oxazolineYield 88.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.28 g (38.7 mmol) of aluminum lithium hydride was suspended in tetrahydrofuran (20 ml). At room temperature, 5.0 g (16.9 mmol) of 4,4-dimethyl-2-(4'-carboxybiphenyl-2-yl)oxazoline was gradually added thereto, followed by stirring for 2 hours. After the reaction liquid was cooled with ice, 100 ml of water 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 4.2 g of the title compound (yield 88%).

Workup

  1. customAfter the reaction liquid
  2. additionwas added
  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-48167aaa38ef429aba6fe470063ead91
Source dataset
uspto-grants-1997_04
Patent number
US05618969

Reaction notes

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