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

HRID 1082011Notes

Reaction equation

HRID 1082011 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 152891614,4-Dimethyl-2-(4'-carboxybiphenyl-2-yl)oxazolineHCID 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 (33.7 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-8b851975cc8a412d8fb169e4e3e70269
Source dataset
uspto-grants-1996_12
Patent number
US05587504

Reaction notes

Loading…