Acetic Anhydride → 1-Acetyl-1H-indol-3-yl acetate

HRID 641886Notes

Reaction equation

HRID 641886 reaction equation
[C:1]([O:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1)(=[O:3])[CH3:2].[C:14](OC(=O)C)(=[O:16])[CH3:15].C(N(CC)CC)C>O1CCCC1.CN(C1C=CN=CC=1)C>[C:1]([O:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([C:14](=[O:16])[CH3:15])[CH:6]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 11841Indoxyl acetate

Product 1

HCID 5836021-Acetyl-1H-indol-3-yl acetate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Into a 500 mL round bottom flask was placed a solution of 1H-indol-3-yl acetate (8 g, 45.69 mmol) in tetrahydrofuran (150 mL). To this was added acetic anhydride (46.6 g, 456.86 mmol). Addition of triethylamine (9.25 g, 91.49 mmol) was next. To the mixture was added DMAP (1.11 g, 9.10 mmol). The resulting solution was allowed to react, with stirring, for 3 hours while the temperature was maintained at reflux in a bath of oil. The reaction progress was monitored by TLC (ethyl acetate/petroleum ether=1:2). The mixture was concentrated by evaporation under vacuum using a rotary evaporator. The resulting solution was diluted with 300 mL of ethyl acetate The resulting mixture was washed 2 times with 150 mL of NaCl(aq.). The mixture was dried over Na2SO4. The residue was purified by eluting through a column with a 20:1 petroleum ether/ethyl acetate solvent system. This resulted in 6.6 g (67%) of 1-acetyl-1H-indol-3-yl acetate as a white solid.

Workup

  1. customInto a 500 mL round bottom flask was placed
  2. customto react
  3. temperaturewas maintained
  4. temperatureat reflux in a bath of oil
  5. concentrationThe mixture was concentrated by evaporation under vacuum
  6. customa rotary evaporator
  7. additionThe resulting solution was diluted with 300 mL of ethyl acetate The resulting mixture
  8. washwas washed 2 times with 150 mL of NaCl(aq.)
  9. dry with materialThe mixture was dried over Na2SO4
  10. customThe residue was purified
  11. washby eluting through a column with a 20:1 petroleum ether/ethyl acetate solvent system
  12. customThis resulted in 6.6 g (67%) of 1-acetyl-1H-indol-3-yl acetate as a white solid

Sources & evidence

ORD record
ord-40cfbfe380a440d6810efc46f510a9c2
Source dataset
uspto-grants-2010_04
Patent number
US07696229B2

Reaction notes

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