Acetyl chloride → 2-Propanone, 1-(4,5-dihydro-2-oxazolyl)-

HRID 435959

Reaction equation

HRID 435959 reaction equation
[CH3:1][C:2]1[O:3][CH2:4][CH2:5][N:6]=1.C([Li])CCC.[C:12](Cl)(=[O:14])[CH3:13]>O1CCCC1>[CH2:1]([C:2]1[O:3][CH2:4][CH2:5][N:6]=1)[C:12]([CH3:13])=[O:14]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 707132-Methyl-2-oxazolineHCID 178418339Butyllithium

Product 1

HCID 836422-Propanone, 1-(4,5-dihydro-2-oxazolyl)-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 8.5 g. (0.1 mole) of 2-methyl-1,3-oxazoline in 85 ml. of dry tetrahydrofuran, and cooled in an acetone-dry ice bath to -60° C., is added 6.4 g. (0.1 mole) of n-butyl lithium and the reaction mixture allowed to stir for 1 hour. To the cloudy solution is then added 7.8 g. (0.1 mole) of acetyl chloride at such a rate that the temperature is maintained below -50° C. The reaction mixture is allowed to warm to room temperature and is then filtered and the solvent removed in vacuo. The desired product is purified by distillation under reduced pressure.

Workup

  1. additionis added 6.4 g
  2. additionTo the cloudy solution is then added 7.8 g
  3. filtrationis then filtered
  4. customthe solvent removed in vacuo
  5. distillationThe desired product is purified by distillation under reduced pressure

Sources & evidence

ORD record
ord-620835d5b0114d35a634cbba05618c46
Source dataset
uspto-grants-1977_02
Patent number
US04007184

Linked notes

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