Benzene → HCID 23333847, compound

HRID 904236Notes

Reaction equation

HRID 904236 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[O:11][CH2:12][C:13]([CH3:16])([CH3:15])[N:14]=2)[CH3:9])=[CH:4][CH:3]=1.Br[C:18]1[S:19][CH:20]=[CH:21][C:22]=1[CH3:23].[Mg].C1C=CC=CC=1>O1CCCC1.[Pd](Cl)Cl.C(O)(=O)C.O>[CH3:23][C:22]1[CH:21]=[CH:20][S:19][C:18]=1[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[O:11][CH2:12][C:13]([CH3:16])([CH3:15])[N:14]=2)[CH3:9])=[CH:4][CH:3]=1

Participants

9

Reactant 4

HCID 241BenzeneHCID 843142-Bromo-3-methylthiopheneHCID 5462224MagnesiumHCID 23333811HCID 23333811, compound

Product 1

HCID 23333847HCID 23333847, compoundYield 93.4%

Reagents, catalysts & solvents 4

HCID 24290Palladium ChlorideCatalystHCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 8.0 g of 2-[1-(4-iodophenyl)ethyl]-4,4-dimethyl-2-oxazoline in 24 ml of anhydrous tetrahydrofuran was added 0.080 g of palladium chloride and the mixture was kept at 60° to 65° C. On the other hand, a Grignard reagent was prepared from 5.2 g of 2-bromo-3-methylthiophene, 0.8 g of magnesium turnings and 15 ml of anhydrous tetrahydrofuran. The Grignard reagent was added dropwise to the above mixture over a period of 30 minutes, while maintaining the temperature at 60° to 65° C. After the addition, the mixture was stirred at the same temperature for one hour to complete the reaction. After removal of the solvent by distillation under reduced pressure, to the residual reaction mixture were added 50 ml of benzene, 50 ml of water and 5 ml of glacial acetic acid, and the mixture was shaken thoroughly. The organic layer was separated, washed with water, dried over anhydrous magnesium sulfate, and freed from the solvent by distillation under reduced pressure to obtain 6.8 g (93.3% yield) of oily 2-[1-[4-(3-methyl-2-thienyl)phenyl]ethyl]-4,4-dimethyl-2-oxazoline.

Workup

  1. customwas kept at 60° to 65° C
  2. temperaturewhile maintaining the temperature at 60° to 65° C
  3. additionAfter the addition
  4. customthe reaction
  5. customAfter removal of the solvent
  6. distillationby distillation under reduced pressure
  7. customto the residual reaction mixture
  8. stirringthe mixture was shaken thoroughly
  9. customThe organic layer was separated
  10. washwashed with water
  11. dry with materialdried over anhydrous magnesium sulfate
  12. distillationfreed from the solvent by distillation under reduced pressure

Sources & evidence

ORD record
ord-b2b31fd962354c86ac1dce977138caee
Source dataset
uspto-grants-1980_10
Patent number
US04230719

Reaction notes

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