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

HRID 341834노트

반응식

HRID 341834 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 74505Methyltriphenyliphosphonium bromide촉매HCID 8028Tetrahydrofuran용매3회

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-8a1affed58ea4164b6e9fac1f1c4b42a
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05856334

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