Quinoline → 5-(4-methoxyphenyl)-5H,6aH-benzo[4,5][1,3]oxazino[3,2-a]quinoline

HRID 1501292ノート

反応式

HRID 1501292 の反応式
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH3:11][O: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>[CH3:11][O:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]2[O:18][CH:2]3[CH:3]=[CH:4][C:5]4[C:10]([N:1]3[C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][C:27]2=3)=[CH:9][CH:8]=[CH:7][CH:6]=4)=[CH:15][CH:14]=1

参加物

7

反応物 5

HCID 7047QuinolineHCID 2855718-Crown-6HCID 312444-MethoxybenzaldehydeHCID 522689Potassium FluorideHCID 33840072-(Trimethylsilyl)phenyl trifluoromethanesulfonate

生成物 1

HCID 1185492995-(4-methoxyphenyl)-5H,6aH-benzo[4,5][1,3]oxazino[3,2-a]quinoline収率 66%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Following the general procedure, treatment of quinoline (0.064g, 59 μL, 0.50 mmol) and 4-methoxybenzaldehyde (0.136 g, 91 μL, 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 rt for 12 h followed by flash column chromatography (Pet. ether/EtOAc=75/25) of the crude reaction mixture afforded 5-(4-methoxyphenyl)-5H,6aH-benzo[4,5][1,3]oxazino[3,2-a]quinoline as a yellow solid (0.112 g, 66% yield, dr determined by 1H NMR analysis of crude reaction mixture is >20:1).

後処理

  1. customat −10° C. to rt
  2. customfor 12 h
  3. customreaction mixture

出典と根拠

ORDレコード
ord-00db8519c4e541c2a151b7acf818ea1e
出典データセット
uspto-grants-2015_12
特許番号
US09206196B1

反応ノート

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