Benzophenone → HCID 102108769, compound

HRID 1501308Notes

Reaction equation

HRID 1501308 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[C:11]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.FC(F)(F)S(O[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[Si](C)(C)C)(=O)=O.[F-].[K+].C1OCCOCCOCCOCCOCCOC1>C1COCC1>[C:12]1([C:11]2([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[O:18][CH:2]3[CH:3]=[CH:4][C:5]4[C:10]([N:1]3[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]2=3)=[CH:9][CH:8]=[CH:7][CH:6]=4)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 5

HCID 3102BenzophenoneHCID 7047QuinolineHCID 2855718-Crown-6HCID 522689Potassium FluorideHCID 33840072-(Trimethylsilyl)phenyl trifluoromethanesulfonate

Product 1

HCID 102108769HCID 102108769, compoundYield 54.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following the general procedure, treatment of quinoline (0.064 g, 59 μL, 0.50 mmol) and benzophenone (0.136 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=95/05) of the crude reaction mixture afforded 5,5-diphenyl-5H,6aH-benzo[4,5][1,3]oxazino[3,2-a]quinoline as a yellow solid (0.105g, 54% yield).

Workup

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

Sources & evidence

ORD record
ord-b95fe09b3f9e4c5881bd30db8f23f601
Source dataset
uspto-grants-2015_12
Patent number
US09206196B1

Reaction notes

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