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

HRID 905026Notes

Reaction equation

HRID 905026 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]>FC(F)(F)S([O-])(=O)=O.[Ag+].C(Cl)Cl>[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

A solution of 33.5 g. (0.148 mole) of 2-(3-ethyl-5-methyl-4-isoxazolyl)-indole in 450 ml. methylene chloride is treated by the portionwise addition of 41.8 g. (0.163 mole) of silver trifluoromethanesulfonate. The resulting suspension is then treated by the dropwise addition of 12.8 g. (0.163 mole) of acetyl chloride in 50 ml. 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 ml. 2 N sodium hydroxide, water and 2 N sodium hydroxide dried over anhydrous magnesium sulfate and evaporated in vacuo to give 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 resulting suspension is then treated by the dropwise addition of 12.8 g
  2. additionThe temperature rises to 35° C. during the addition
  3. additionAfter the addition
  4. filtrationfiltered
  5. washThe filtrate is washed with 150 ml
  6. dry with material2 N sodium hydroxide, water and 2 N sodium hydroxide dried over anhydrous magnesium sulfate
  7. customevaporated in vacuo
  8. customto give an oil
  9. customThe oil is crystallized from ether

Sources & evidence

ORD record
ord-ed719ab194414d2f925af7c0b868bae5
Source dataset
uspto-grants-1983_12
Patent number
US04421752

Reaction notes

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