Ethyl Acetate → 5,6-dihydro-6-methylene-2-(2-phenylethyl)-4H-imidazo[4,5,1-ij]quinoline

HRID 341834ノート

反応式

HRID 341834 の反応式
[CH3:1][C:2]([CH3:5])([O-])[CH3:3].[K+].[C:7]1([CH2:13][CH2:14][C:15]2[N:25]3[C:26]4C(C(=O)C[CH2:24]3)=[CH:20][CH:19]=[CH:18][C:17]=4[N:16]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(=O)([O-])O.[Na+].C(OCC)(=O)C>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[CH2:1]=[C:2]1[C:5]2[C:26]3=[C:17]([N:16]=[C:15]([CH2:14][CH2:13][C:7]4[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=4)[N:25]3[CH2:24][CH2:3]1)[CH:18]=[CH:19][CH:20]=2

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 158384624,5-dihydro-2-(2-phenylethyl)-6H-imidazo[4,5,1-ij]-quinolin-6-oneHCID 23665647Potassium tert-butoxide

生成物 1

HCID 158384645,6-dihydro-6-methylene-2-(2-phenylethyl)-4H-imidazo[4,5,1-ij]quinoline収率 82.6%

試薬・触媒・溶媒 2

HCID 74505Methyltriphenyliphosphonium bromide触媒HCID 8028Tetrahydrofuran溶媒3 回

実験手順

Methyltriphenylphosphonium bromide (1.29 g) was suspended in anhydrous tetrahydrofuran (10 mL) and a solution of potassium t-butoxide (0.45 g) in tetrahydrofuran (10 mL) was added dropwise at room temperature, followed by stirring for 1 hr at room temperature. Subsequently, 0.50 g of 4,5-dihydro-2-(2-phenylethyl)-6H-imidazo[4,5,1-ij]quinolin-6-one obtained in Example 1 was dissolved in anhydrous tetrahydrofuran (10 mL) and the solution was added dropwise and the mixture was stirred at room temperature for 1 hr. To the reaction solution, a saturated aqueous solution of sodium hydrogencarbonate (50 mL) and ethyl acetate (50 mL) were added and then two layers were separated. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: dichloromethane/ethyl acetate) to yield the titled compound as colorless crystals (0.41 g).

後処理

  1. additionthe solution was added dropwise
  2. stirringthe mixture was stirred at room temperature for 1 hr
  3. customtwo layers were separated
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent: dichloromethane/ethyl acetate)

出典と根拠

ORDレコード
ord-8a1affed58ea4164b6e9fac1f1c4b42a
出典データセット
uspto-grants-1999_01
特許番号
US05856334

反応ノート

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