HCID 10632456, compound → Oxazole, 5-methyl-2-phenyl-4-(2-propynyl)-

HRID 2253958Notes

Reaction equation

HRID 2253958 reaction equation
[C:1]([NH:9][CH:10]([C:14](=[O:16])[CH3:15])[CH2:11][C:12]#[CH:13])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>FC(F)(F)C(OC(=O)C(F)(F)F)=O.FC(F)(F)C(O)=O>[CH3:15][C:14]1[O:16][C:1]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[N:9][C:10]=1[CH2:11][C:12]#[CH:13]

Participants

4

Reactant 1

HCID 10632456HCID 10632456, compound

Product 1

HCID 10535929Oxazole, 5-methyl-2-phenyl-4-(2-propynyl)-Yield 101.4%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 9845Trifluoroacetic anhydrideSolvent

Procedure

A solution of 4-benzoylamino-1-hexyn-5-one (30 g, 0.14 mol) in trifluoroacetic anhydride (100 ml) and trifluoroacetic acid (200 ml) was heated to 35°-40° C. for 6 hours. The solution was concentrated and the residue taken up in ethyl acetate (400 ml). To this solution was added saturated sodium bicarbonate solution (400 ml) followed by solid sodium bicarbonate until the water layer became neutral. The layers were separated, the organic layer was washed with brine, dried over magnesium sulfate and concentrated to give a brown oil (28 g) which was used as such.

Workup

  1. concentrationThe solution was concentrated
  2. additionTo this solution was added saturated sodium bicarbonate solution (400 ml)
  3. customThe layers were separated
  4. washthe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-60f1d8eace8746eaa97a0aff130d5b96
Source dataset
uspto-grants-1993_08
Patent number
US05232945

Reaction notes

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