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

HRID 641886

반응식

HRID 641886 반응식
[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]

참가 물질

6

반응물 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 11841Indoxyl acetate

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-40cfbfe380a440d6810efc46f510a9c2
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07696229B2

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