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Sodium hydride → ethyl (E)-3-[1-(1-methylethyl)-1,2,3,4-tetrahydroquinolin-6-yl]-2-fluoro-2-butenoate

HRID 2229173
ノート
印刷プレビュー

反応式

HRID 2229173 の反応式
[H-].[Na+].[F:3][CH:4](P(OCC)(OCC)=O)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH3:18][CH:19]([N:21]1[C:30]2[C:25](=[CH:26][C:27]([C:31](=O)[CH3:32])=[CH:28][CH:29]=2)[CH2:24][CH2:23][CH2:22]1)[CH3:20].[Cl-].[NH4+]>CN(C)C=O>[CH3:20][CH:19]([N:21]1[C:30]2[C:25](=[CH:26][C:27](/[C:31](/[CH3:32])=[C:4](/[F:3])\[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:28][CH:29]=2)[CH2:24][CH2:23][CH2:22]1)[CH3:18]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 2734865Triethyl 2-fluoro-2-phosphonoacetateHCID 107751501-[1-(1-Methylethyl)-1,2,3,4-tetrahydroquinolin-6-yl)ethanone

生成物 1

HCID 10852120ethyl (E)-3-[1-(1-methylethyl)-1,2,3,4-tetrahydroquinolin-6-yl]-2-fluoro-2-butenoate

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

実験手順

450 mg (60%, 12 mmol) of sodium hydride was suspended in 10 ml of N,N-dimethylformamide. 3.3.g (14 mmol) of ethyl 2-fluoro-diethylphosphonoacetate was dropped into the suspension under cooling with ice. The obtained mixture was stirred under cooling with ice for 30 minutes, followed by the addition of 2.0 g (9.2 mmol) of 1-[1-(1-methylethyl)-1,2,3,4-tetrahydroquinolin-6-yl)ethanone. The obtained mixture was stirred under cooling with ice for one hour, followed by the addition of an aqueous solution of ammonium chloride. The obtained mixture was extracted with ethyl acetate, and the organic phase was washed with a saturated aqueous solution of common salt, dried over anhydrous magnesium sulfate and concentrated in a vacuum. The residue was purified by silica gel column chromatography to give 2.3 g of the title compound as a colorless oil.

後処理

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice for 30 minutes
  3. stirringThe obtained mixture was stirred
  4. temperatureunder cooling with ice for one hour
  5. extractionThe obtained mixture was extracted with ethyl acetate
  6. washthe organic phase was washed with a saturated aqueous solution of common salt
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated in a vacuum
  9. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-bb196681e37144ebbe43c2d14973748a
出典データセット
uspto-grants-2002_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06420363B1

反応ノート

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