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Sodium Hydroxide → 2-Fluoro-4-(8,8-dimethl-5-oxo-5,6,7,8-tetrahydro-naphthalen-2yl-ethynyl)-benzoic Acid

HRID 841565
ノート
印刷プレビュー

反応式

HRID 841565 の反応式
C([O:3][C:4](=[O:27])[C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:22]=[CH:21][C:20]3[C:19](=[O:23])[CH2:18][CH2:17][C:16]([CH3:25])([CH3:24])[C:15]=3[CH:14]=2)=[CH:7][C:6]=1[F:26])C.[OH-].[Na+]>C(O)C.CO.O1CCCC1>[F:26][C:6]1[CH:7]=[C:8]([C:11]#[C:12][C:13]2[CH:22]=[CH:21][C:20]3[C:19](=[O:23])[CH2:18][CH2:17][C:16]([CH3:25])([CH3:24])[C:15]=3[CH:14]=2)[CH:9]=[CH:10][C:5]=1[C:4]([OH:27])=[O:3]
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 2

HCID 14798Sodium HydroxideHCID 129717122-Fluoro-4-(8,8-dimethyl-5-oxo-5,6,7,8-tetrahydronaphthalen-2-ylethynyl)benzoic acid ethyl ester2 回

生成物 1

HCID 99675692-Fluoro-4-(8,8-dimethl-5-oxo-5,6,7,8-tetrahydro-naphthalen-2yl-ethynyl)-benzoic Acid収率 27.1%

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 887Methanol
溶媒
HCID 8028Tetrahydrofuran溶媒

反応条件

温度
70 °C

実験手順

A solution of 2-fluoro-4-(8,8-dimethyl-5-oxo-5,6,7,8-tetrahydro-naphthalen-2-ylethynyl)benzoic acid ethyl ester (Compound 9, 0.1 g, 0.274 mmol) in ethanol(4 mL), methanol (2 mL) and tetrahydrofuran (2 mL) was treated with 1M aqueous sodium hydroxide solution and heated at 70° C. for 1 h. The volatiles were distilled off in vacuo and the residue was diluted with water and dilute hydrochloric acid and extracted with ethyl acetate (×2). The combined organic extract was dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to afford a solid that was recrystallized from hot aqueous acetonitrile to afford the title compound (0.025 g, 27%).

後処理

  1. distillationThe volatiles were distilled off in vacuo
  2. additionthe residue was diluted with water and dilute hydrochloric acid
  3. extractionextracted with ethyl acetate (×2)
  4. extractionThe combined organic extract
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customto afford a solid
  9. customthat was recrystallized from hot aqueous acetonitrile

出典と根拠

ORDレコード
ord-c401c5cf29314519a672e527482c4c03
出典データセット
uspto-grants-2002_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06369261B1

反応ノート

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