Dichloromethane → 4,4-Dimethyl-2-(4'-methoxycarbonylbiphenyl-2-yl)oxazoline

HRID 743752

Reaction equation

HRID 743752 reaction equation
[CH3:1][C:2]1([CH3:22])[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]([OH:21])=[O:20])=[CH:15][CH:14]=2)=[N:3]1.S(Cl)(Cl)=O.[CH2:27](Cl)Cl>>[CH3:1][C:2]1([CH3:22])[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]([O:21][CH3:27])=[O:20])=[CH:15][CH:14]=2)=[N:3]1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 15289161HCID 15289161, compound

Product 1

HCID 153808774,4-Dimethyl-2-(4'-methoxycarbonylbiphenyl-2-yl)oxazolineYield 91%

Procedure

10.0 g (33.8 mmol) of 4,4-dimethyl-2-(4'-carboxybiphenyl-2-yl)oxazoline was dissolved in methylene chloride (200 ml). 4.8 g (40.3 mmol) of thionyl chloride was added thereto, followed by stirring at room temperature for 2 hours. The reaction liquid was subjected to vacuum concentration. Methanol (100 ml) was added to the residue, followed by stirring for 3 hours. After distilling out the solvent under a reduced pressure, methylene chloride and a saturated aqueous solution of sodium hydrogencarbonate were added to the residue and obtained mixture was caused liquid-liquid separation. After washing with water and drying, vacuum concentration was conducted. The residue was purified by silica gel column chromatography (an ethyl acetate/n-hexane system) to give 9.53 g of the title compound as an oil (yield 91%).

Workup

  1. customThe reaction liquid
  2. concentrationwas subjected to vacuum concentration
  3. additionMethanol (100 ml) was added to the residue
  4. stirringby stirring for 3 hours
  5. distillationAfter distilling out the solvent under a reduced pressure, methylene chloride
  6. additiona saturated aqueous solution of sodium hydrogencarbonate were added to the residue
  7. customobtained mixture
  8. customliquid-liquid separation
  9. washAfter washing with water
  10. customdrying
  11. concentrationvacuum concentration
  12. customThe residue was purified by silica gel column chromatography (an ethyl acetate/n-hexane system)

Sources & evidence

ORD record
ord-bd655b34f4f2400baf2bd2a4e5349b5f
Source dataset
uspto-grants-1996_09
Patent number
US05557002

Linked notes

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