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Water → [11-(2-Ethylhexyl)-8-(2,4,6-trimethylbenzoyl)-11H-benzo[a]carbazole-5-yl]-[4-(2,2,3,3-tetrafluoropropoxy)-phenyl]-methane oxime

HRID 2172368
ノート
印刷プレビュー

反応式

HRID 2172368 の反応式
[CH2:1]([CH:3]([CH2:42][CH2:43][CH2:44][CH3:45])[CH2:4][N:5]1[C:17]2[C:12](=[CH:13][C:14]([C:22](=O)[C:23]3[CH:28]=[CH:27][C:26](F)=[CH:25][CH:24]=3)=[C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]3=2)[C:11]2[C:6]1=[CH:7][CH:8]=[C:9]([C:31]([C:33]1[C:38]([CH3:39])=[CH:37][C:36]([CH3:40])=[CH:35][C:34]=1[CH3:41])=O)[CH:10]=2)[CH3:2].[F:46][C:47]([F:53])([CH:50]([F:52])[F:51])[CH2:48]O.[OH-:54].[Na+].[OH2:56].[N:57]1C=CC=CC=1>>[CH2:1]([CH:3]([CH2:42][CH2:43][CH2:44][CH3:45])[CH2:4][N:5]1[C:17]2[C:12](=[CH:13][C:14]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([O:54][CH2:48][C:47]([F:53])([F:46])[CH:50]([F:52])[F:51])=[CH:25][CH:24]=3)=[C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]3=2)[C:11]2[C:6]1=[CH:7][CH:8]=[C:9]([C:31](=[N:57][OH:56])[C:33]1[C:38]([CH3:39])=[CH:37][C:36]([CH3:40])=[CH:35][C:34]=1[CH3:41])[CH:10]=2)[CH3:2]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 5

HCID 962WaterHCID 1049PyridineHCID 64412,2,3,3-Tetrafluoro-1-propanolHCID 14798Sodium HydroxideHCID 67130099[11-(2-Ethylhexyl)-5-(4-fluorobenzoyl)-11H-benzo[a]carbazol-8-yl]-(2,4,6-trimethylphenyl)-methanone

生成物 1

HCID 86690533
[11-(2-Ethylhexyl)-8-(2,4,6-trimethylbenzoyl)-11H-benzo[a]carbazole-5-yl]-[4-(2,2,3,3-tetrafluoropropoxy)-phenyl]-methane oxime
収率 51%

反応条件

温度
70 °C

実験手順

To [11-(2-ethylhexyl)-5-(4-fluorobenzoyl)-11H-benzo[a]carbazol-8-yl]-(2,4,6-trimethylphenyl)-methanone (1.29 g, 2.16 mmol) in pyridine (3 ml) are added 2,2,3,3-tetrafluoro-1-propanol (0.43 g, 3.24 mmol) and sodium hydroxide (0.13 g, 3.32 mmol). The mixture is stirred at 70° C. for 23 hours, and then it is stirred at 120° C. for 24 hours. After the reaction mixture is cooled at room temperature, it is poured into water, and then the crude product is extracted with AcOEt, and washed with water and brine. After drying over MgSO4 and concentration, the crude product is purified by column chromatography on silica gel eluting with CH2Cl2 to obtain a white solid (0.80 g, 51%). The product is composed of an isomeric mixture, and the structure is confirmed by 1H-NMR spectrum (CDCl3) δ [ppm]: 0.79-0.99 (m), 1.24-1.52 (m), 2.05 (s), 2.13 (s), 2.35 (s), 2.37 (s), 4.31 (t), 4.73-4.77 (m), 5.90-6.16 (m), 6.83 (d), 6.87 (d), 6.92 (s), 6.94 (s), 7.50-7.73 (m), 7.88 (d), 8.00 (s), 8.11 (br), 8.19 (s), 8.41 (br), 8.55 (d), 8.62 (d); 19F-NMR spectrum (CDCl3). δ [ppm] −125.04, −124.90.

後処理

  1. stirringit is stirred at 120° C. for 24 hours
  2. temperatureAfter the reaction mixture is cooled at room temperature
  3. extractionthe crude product is extracted with AcOEt
  4. washwashed with water and brine
  5. dry with materialAfter drying over MgSO4 and concentration
  6. customthe crude product is purified by column chromatography on silica gel eluting with CH2Cl2

出典と根拠

ORDレコード
ord-48914a2ea968453a939c60f0ff99de91
出典データセット
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09051397B2

反応ノート

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