Acetic Acid → Methyl 2-(3-(3-((7-chloro-2-quinolinyl)methoxy)phenyl)-2-propenyl)benzoate

HRID 258470노트

반응식

HRID 258470 반응식
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH2:12][O:13][C:14]3[CH:15]=[C:16]([CH:20]=[CH:21][CH2:22][C:23]4[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=4[CH:25]=[O:26])[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1.[C-]#N.[Na+].C[C:35](O)=[O:36]>CO.C1COCC1.O=[Mn]=O>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH2:12][O:13][C:14]3[CH:15]=[C:16]([CH:20]=[CH:21][CH2:22][C:23]4[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=4[C:25]([O:36][CH3:35])=[O:26])[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1

참가 물질

6

반응물 3

HCID 176Acetic AcidHCID 8929Sodium CyanideHCID 536926242-(3-(3-((7-Chloro-2-quinolinyl)methoxy)phenyl)-2-propenyl)benzaldehyde

생성물 1

HCID 53936847Methyl 2-(3-(3-((7-chloro-2-quinolinyl)methoxy)phenyl)-2-propenyl)benzoate수율 84.4%

시약·촉매·용매 2

HCID 14801Manganese dioxide촉매HCID 21899815MeOH tetrahydrofuran용매

실험 절차

To a solution of the aldehyde of Step 6 (17.26 g, 41.7 mmol) in 1.5 L of MeOH:THF 2:1, NaCN (20 g, 408 mmol), AcOH (5.7 mL, 98.9 mmol) and activated MnO2 (90 g, 1.01 mol) were added and the mixture was stirred for 16 h. The inorganic solid was then removed by filtration and washed with EtOAc. To the combined organic phases, 25% aq NH4OAc (1.7 L) was added. The two phases were separated and the aqueous layer was reextracted with EtOAc. The organic phases were washed with brine and dried over Na2SO4. Flash chromatography of the residue on silica with toluene and EtOAc:toluene 2.5:97.5 afforded 15.63 g (84%) of the title ester.

후처리

  1. customThe inorganic solid was then removed by filtration
  2. washwashed with EtOAc
  3. additionTo the combined organic phases, 25% aq NH4OAc (1.7 L) was added
  4. customThe two phases were separated
  5. washThe organic phases were washed with brine
  6. dry with materialdried over Na2SO4

출처 및 근거

ORD 기록
ord-263e7617ce2648ffb5e122e737da3f9f
출처 데이터셋
uspto-grants-1993_11
특허 번호
US05266568

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