Acetic Acid → 1-[2-(3-Ethyl-5-methyl-1,2-oxazol-4-yl)-1H-indol-3-yl]ethan-1-one

HRID 1380573Notes

Reaction equation

HRID 1380573 reaction equation
[C:1](O)(=[O:3])[CH3:2].P(=O)(O)(O)O.FC(F)(F)C(OC(=O)C(F)(F)F)=O.[CH2:23]([C:25]1[C:29]([C:30]2[NH:31][C:32]3[C:37]([CH:38]=2)=[CH:36][CH:35]=[CH:34][CH:33]=3)=[C:28]([CH3:39])[O:27][N:26]=1)[CH3:24]>C(#N)C.CCOCC>[C:1]([C:38]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[NH:31][C:30]=1[C:29]1[C:25]([CH2:23][CH3:24])=[N:26][O:27][C:28]=1[CH3:39])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 1004Phosphoric AcidHCID 9845Trifluoroacetic anhydrideHCID 130386862-(3-Ethyl-5-methyl-1,2-oxazol-4-yl)-1H-indole

Product 1

HCID 128514531-[2-(3-Ethyl-5-methyl-1,2-oxazol-4-yl)-1H-indol-3-yl]ethan-1-one

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent2×

Procedure

To a mixture of 0.77 milliliters (13.45 m mole) of acetic acid and 0.17 grams (1.47 m mole) of 85% phosphoric acid in 10 milliliters of acetonitrile is added, at room temperature, 1.9 milliliters (13.45 m mole) of trifluoroacetic acid anhydride. The mixture is stirred for 15 minutes and then treated by dropwise addition with 1.0 grams (4.42 m mole) of 2-(3-ethyl-5-methyl-isoxazolyl)-indole in 10 milliliters acetonitrile. The mixture is stirred for 31/2 hours at room temperature and then poured onto water and extracted with ether. The ether extracts are dried over magnesium sulfate, filtered and evaporated in vacuo. The resulting oil is filtered through silica gel using 10% methanol/methylene chloride. The solvent is evaporated, and the oil obtained is dissolved in ether. The solution is washed with 10% sodium bicarbonate solution, decolorized with charcoal, dried over magnesium sulfate and evaporated in vacuo. The resulting oil crystallizes upon treatment with ether to give 3-acetyl-2-(3-ethyl-5-methyl-4 -isoxazolyl)-indole, m.p. 170°-171°.

Workup

  1. additionis added, at room temperature
  2. stirringThe mixture is stirred for 31/2 hours at room temperature
  3. additionpoured onto water
  4. extractionextracted with ether
  5. dry with materialThe ether extracts are dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. filtrationThe resulting oil is filtered through silica gel using 10% methanol/methylene chloride
  9. customThe solvent is evaporated
  10. customthe oil obtained
  11. washThe solution is washed with 10% sodium bicarbonate solution
  12. dry with materialdried over magnesium sulfate
  13. customevaporated in vacuo
  14. customThe resulting oil crystallizes upon treatment with ether

Sources & evidence

ORD record
ord-de3595eba7a84138be1d8ad8b31ecc6e
Source dataset
uspto-grants-1986_04
Patent number
US04582848

Reaction notes

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