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Trifluoroacetic acid → Methyl 2-(4-fluoro-3-nitrophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate

HRID 1801293
ノート
印刷プレビュー

反応式

HRID 1801293 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:17]([CH3:19])([CH3:18])[CH:16](O)[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:21]([O:23][CH3:24])=[O:22])[CH:14]=3)[NH:9]2)=[CH:4][C:3]=1[N+:25]([O-:27])=[O:26].C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:17]([CH3:19])([CH3:18])[CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:21]([O:23][CH3:24])=[O:22])[CH:14]=3)[NH:9]2)=[CH:4][C:3]=1[N+:25]([O-:27])=[O:26]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 67442290Methyl 2-(4-fluoro-3-nitrophenyl)-4-hydroxy-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate

生成物 1

HCID 67442620Methyl 2-(4-fluoro-3-nitrophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate収率 75%

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒
2 回

実験手順

To an ice-cooled mixture of methyl 2-(4-fluoro-3-nitrophenyl)-4-hydroxy-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate (3.39 g, 9.06 mmol) and triethylsilane (3.06 g, 26.3 mmol) in dichloromethane (180 mL) was added a solution of trifluoroacetic acid (4.24 g, 37.1 mmol) in dichloromethane (90 mL) dropwise during 3 hours. After addition, ice-bath was removed and the reaction mixture was stirred at room temperature for 44 hours. Solid sodium carbonate was added and stirred for 15 minutes, filtered, and concentrated. The oil residue was purified by column (silica gel, petroleum ether/ethyl acetate=10:1 to 1:1 due to bad solubility) to afford methyl 2-(4-fluoro-3-nitrophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate 2.44 mg (75%) as a yellow solid.

後処理

  1. additionAfter addition, ice-bath
  2. customwas removed
  3. additionSolid sodium carbonate was added
  4. stirringstirred for 15 minutes
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe oil residue was purified by column (silica gel, petroleum ether/ethyl acetate=10:1 to 1:1 due to bad solubility)

出典と根拠

ORDレコード
ord-5d463d279ed1406fa73744d63b28516e
出典データセット
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08344137B2

反応ノート

読み込み中…

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