Water → 1,7-Diacetyl-4-methoxyindoline

HRID 1884405ノート

反応式

HRID 1884405 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

HCID 232464691,7-Diacetyl-4-methoxyindoline収率 54%

試薬・触媒・溶媒 3

HCID 111,2-Dichloroethane溶媒HCID 3283Diethyl Ether溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
50 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-15423bcfc264408f91a5252ab45575f7
出典データセット
uspto-grants-2004_07
特許番号
US06765014B1

反応ノート

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