4-Toluenesulfonyl chloride → 4,4-Dimethyl-2-(4'-p-toluenesulfonyloxymethylbiphenyl-2-yl)oxazoline

HRID 744966Notes

Reaction equation

HRID 744966 reaction equation
[H-].[Na+].[CH3:3][C:4]1([CH3:23])[CH2:8][O:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]2[CH:20]=[CH:19][C:18]([CH2:21][OH:22])=[CH:17][CH:16]=2)=[N:5]1.[C:24]1([CH3:34])[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1.[Cl-].[NH4+]>O1CCCC1>[CH3:3][C:4]1([CH3:23])[CH2:8][O:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]2[CH:16]=[CH:17][C:18]([CH2:21][O:22][S:30]([C:27]3[CH:28]=[CH:29][C:24]([CH3:34])=[CH:25][CH:26]=3)(=[O:32])=[O:31])=[CH:19][CH:20]=2)=[N:5]1

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 110658764,4-Dimethyl-2-(4'hydroxymethylbiphenyl-2-yl)oxazoline

Product 1

HCID 153808794,4-Dimethyl-2-(4'-p-toluenesulfonyloxymethylbiphenyl-2-yl)oxazolineYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

0.34 g (8.5 mmol) of a 60% oily sodium hydride was suspended in tetrahydrofuran (20 ml). A solution of 2.0 g (7.1 mmol) of 4,4-dimethyl-2-(4'-hydroxymethylbiphenyl-2-yl)oxazoline in tetrahydrofuran (30 ml) was dropwise added thereto at room temperature, followed by further stirring at room temperature for one hour. After the reaction liquid was cooled with ice, a solution of 1.6 g (8.4 mmol) of p-toluenesulfonyl chloride in tetrahydrofuran (20 ml) was dropwise added thereto. After stirring for 3 hours as such, the reaction liquid was poured into a saturated aqueous solution of ammonium chloride, 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 1.7 g of the title compound as an oil (yield 55%).

Workup

  1. customat room temperature
  2. customAfter the reaction liquid
  3. temperaturewas cooled with ice
  4. stirringAfter stirring for 3 hours as such,
  5. customthe reaction liquid
  6. extractionfollowed by the extraction with chloroform
  7. washAfter washing with water
  8. customdrying
  9. concentrationvacuum concentration
  10. customThe residue was purified by silica gel column chromatography (a n-hexane/ethyl acetate system)

Sources & evidence

ORD record
ord-355f6135b5d746ebafb58ae165f0d30d
Source dataset
uspto-grants-1996_09
Patent number
US05559236

Reaction notes

Loading…