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

HRID 258470Notes

Reaction equation

HRID 258470 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-263e7617ce2648ffb5e122e737da3f9f
Source dataset
uspto-grants-1993_11
Patent number
US05266568

Reaction notes

Loading…