Valeryl chloride → HCID 14537429, compound

HRID 1607715Notes

Reaction equation

HRID 1607715 reaction equation
[CH3:1][C:2]1[NH:3][C:4](=[O:7])[O:5][CH:6]=1.[Cl-].[Al+3].[Cl-].[Cl-].[C:12](Cl)(=[O:17])[CH2:13][CH2:14][CH2:15][CH3:16]>C(Cl)Cl>[C:12]([C:6]1[O:5][C:4](=[O:7])[NH:3][C:2]=1[CH3:1])(=[O:17])[CH2:13][CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 61186Valeryl chlorideHCID 6451240Aluminum(III) ChlorideHCID 145374264-Methyl-1,3-oxazol-2(3H)-one

Product 1

HCID 14537429HCID 14537429, compoundYield 39.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Six grams (0.06 mol) of 4-methyl-2(3H)-oxazolone and 24.2 g (0.182 mol) aluminum chloride were suspended in 250 ml methylene chloride. To this mixture was added dropwise 8.3 g (0.069 mol) n-pentanoyl chloride. The mixture was stirred and refluxed 15 hours, cooled and poured into ice water. The methylene chloride layer was isolated, washed with sodium bicarbonate solution and water. The methylene chloride solution was dried and solvent evaporated to give a residue which was recrystallized two times from ethyletherpentane to give 4.3 g (39%) of title compound; m.p. 92°-94°.

Workup

  1. temperaturerefluxed 15 hours
  2. temperaturecooled
  3. washwashed with sodium bicarbonate solution and water
  4. dry with materialThe methylene chloride solution was dried
  5. customsolvent evaporated
  6. customto give a residue which
  7. customwas recrystallized two times from ethyletherpentane

Sources & evidence

ORD record
ord-255c650ed7e844239841e08123c31d92
Source dataset
uspto-grants-1989_09
Patent number
US04866182

Reaction notes

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