4-Chlorobenzaldehyde → HCID 118549276, compound

HRID 1501302Notes

Reaction equation

HRID 1501302 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[Cl:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][CH:14]=1.FC(F)(F)S(O[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[Si](C)(C)C)(=O)=O.[F-].[K+].C1OCCOCCOCCOCCOCCOC1>C1COCC1>[Cl:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]2[O:18][CH:4]3[CH:3]=[C:2]([CH3:1])[C:11]4[C:6]([N:5]3[C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][C:27]2=3)=[CH:7][CH:8]=[CH:9][CH:10]=4)=[CH:15][CH:14]=1

Participants

7

Reactant 5

HCID 77264-ChlorobenzaldehydeHCID 102854-MethylquinolineHCID 2855718-Crown-6HCID 522689Potassium FluorideHCID 33840072-(Trimethylsilyl)phenyl trifluoromethanesulfonate

Product 1

HCID 118549276HCID 118549276, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following the general procedure, treatment of 4-methylquinoline (0.073 g, 66 μL, 0.50 mmol) and 4-chlorobenzaldehyde (0.105 g, 0.75 mmol) with 2-(trimethylsilyl)phenyl trifluoromethanesulfonate (0.179 g, 146 μL, 0.60 mmol) in the presence of KF (0.070 g, 1.2 mmol) and 18-crown-6 (0.317 g, 1.2 mmol) in THF (2.0 mL) at −10° C. to room temperature for 12 hrs followed by flash column chromatography (Pet. ether/EtOAc=50/50) of the crude reaction mixture afforded 5-(4-chlorophenyl)-8-methyl-5H,6aH-benzo[4,5][1,3]oxazino[3,2-a]quinoline as inseparable mixture of diastereomers as a white solid (0.090 g, 50% yield, dr determined by 1H NMR analysis of crude reaction mixture is 3:1).

Workup

  1. customat −10° C. to room temperature
  2. customfor 12 hrs
  3. customreaction mixture

Sources & evidence

ORD record
ord-b686f9279b8e49b6b86a5e7ab92d6062
Source dataset
uspto-grants-2015_12
Patent number
US09206196B1

Reaction notes

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