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

HRID 485322Notes

Reaction equation

HRID 485322 reaction equation
[CH2:1]([C:3]1[C:7]([C:8]2[NH:9][C:10]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][CH:11]=3)=[C:6]([CH3:17])[O:5][N:4]=1)[CH3:2].[C:18](Cl)(=[O:20])[CH3:19]>C(Cl)Cl.FC(F)(F)S([O-])(=O)=O.[Ag+]>[CH2:1]([C:3]1[C:7]([C:8]2[NH:9][C:10]3[C:15]([C:16]=2[C:18](=[O:20])[CH3:19])=[CH:14][CH:13]=[CH:12][CH:11]=3)=[C:6]([CH3:17])[O:5][N:4]=1)[CH3:2]

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 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 76223Silver(I) trifluoromethanesulfonateCatalystHCID 6344DichloromethaneSolvent2×

Procedure

In the alternate procedure, 41.8 grams (0.163 moles) of silver trifluoromethanesulfonate is added portionwise to a solution of 33.5 grams (0.148 mole) of 2-(3-ethyl-5-methyl-4-isoxazolyl)-indole in 450 milliliters of methylene chloride. The resulting suspension is then treated by dropwise addition with 12.8 grams (0.163 moles) of acetyl chloride in 50 milliliters of methylene chloride. The temperature rises to 35° C. during the addition. After the addition is complete the mixture is stirred at room temperature for 4 hours and then filtered. The filtrate is washed with 150 milliliters of of 2N sodium hydroxide, water and 2N sodium hydroxide, then dried over anhydrous magnesium sulfate and finally evaporated in vacuo to yield an oil. The oil is crystallized from ether to give 2-(3-ethyl-5-methyl-4-isoxazolyl)-3-acetyl indole, m.p. 170°-173° C.

Workup

  1. additionThe temperature rises to 35° C. during the addition
  2. additionAfter the addition
  3. filtrationfiltered
  4. washThe filtrate is washed with 150 milliliters of of 2N sodium hydroxide, water and 2N sodium hydroxide
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customfinally evaporated in vacuo
  7. customto yield an oil
  8. customThe oil is crystallized from ether

Sources & evidence

ORD record
ord-3ce211d86e0d4378afb946aa4246f088
Source dataset
uspto-grants-1985_08
Patent number
US04536499

Reaction notes

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