Water → 1,7-Diacetyl-4-methoxyindoline

HRID 1884405노트

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HRID 1884405 반응식
[C:1]([N:4]1[C:12]2[C:7](=[C:8]([O:13][CH3:14])[CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[C:15](Cl)(=[O:17])[CH3:16].[Al+3].[Cl-].[Cl-].[Cl-].O>ClCCCl.CCOCC.CCOC(C)=O>[C:1]([N:4]1[C:12]2[C:7](=[C:8]([O:13][CH3:14])[CH:9]=[CH:10][C:11]=2[C:15](=[O:17])[CH3:16])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

참가 물질

8

반응물 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 235059691-Acetyl-4-methoxyindoline

생성물 1

HCID 232464691,7-Diacetyl-4-methoxyindoline수율 54%

시약·촉매·용매 3

HCID 111,2-Dichloroethane용매HCID 3283Diethyl Ether용매HCID 8857Ethyl Acetate용매

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온도
50 °C

실험 절차

To a solution of 1-acetyl-4-methoxyindoline (4.02 g, 21 mmol) in dry 1,2-dichloroethane (30 ml) cooled in ice was added acetyl chloride (2.1 ml, 30 mmol). Powdered anhydrous AlCl3 (8.4 g, 63 mmol) was added portionwise with stirring. The mixture was stirred at rt overnight, then warmed to 50° C. for 2 h. The red/brown slurry was poured into acidified cold water (200 ml) and extracted with CH2Cl2. The combined organic phases were washed with 0.5 M aq. NaOH and brine, dried and evaporated to give a brown oil. Flash chromatography (EtOAc) followed by trituration with Et2O afforded 22 as pale yellow needles (2.22 g, 54%), mp 88-89° C., (Found: C, 66.89; H, 6.50; N, 5.95. C13H15NO3 requires C, 66.94; H, 6.48; N, 6.00%); δH (90 MHz) 7.33 (1 H, d, J 8.3, H-5), 6.61 (1 H, d, H-6), 4.17 (2 H, t, J 8.1, H-2), 3.85 (3 H, s, OMe), 3.05 (2 H, t, 3-H), 2.44 (3 H, s, 7-Ac) and 2.21 (3 H, s, N-Ac).

후처리

  1. stirringThe mixture was stirred at rt overnight
  2. additionThe red/brown slurry was poured
  3. extractionextracted with CH2Cl2
  4. washThe combined organic phases were washed with 0.5 M aq. NaOH and brine
  5. customdried
  6. customevaporated
  7. customto give a brown oil

출처 및 근거

ORD 기록
ord-15423bcfc264408f91a5252ab45575f7
출처 데이터셋
uspto-grants-2004_07
특허 번호
US06765014B1

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