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Hydrochloric Acid → 5,5,5-Trifluoro-2-[6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-pentanal

HRID 1669306
ノート
印刷プレビュー

反応式

HRID 1669306 の反応式
[F:1][C:2]([F:26])([F:25])[CH2:3][CH2:4][C:5]([C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=2)=[N:13][CH:14]=1)=[CH:6][O:7]C.O1CCCC1.Cl.[OH-].[Na+]>C(OCC)C>[F:26][C:2]([F:1])([F:25])[CH2:3][CH2:4][CH:5]([C:9]1[CH:14]=[N:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:22])([F:23])[F:24])=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)[CH:6]=[O:7]
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 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 866203565-(4,4,4-Trifluoro-1-methoxymethylene-butyl)-2-(4-trifluoromethyl-phenyl)-pyridine

生成物 1

HCID 866203575,5,5-Trifluoro-2-[6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-pentanal収率 91.7%

試薬・触媒・溶媒 1

HCID 3283
Diethyl Ether
溶媒

実験手順

A solution of 5-(4,4,4-trifluoro-1-methoxymethylene-butyl)-2-(4-trifluoromethyl-phenyl)-pyridine (4.1 g, 10.9 mmol) and tetrahydrofuran (50 mL) is treated with concentrated hydrochloric acid (5 mL) and heated to reflux under nitrogen. The reaction is monitored by HPLC and allowed to cool upon completion. The solution is neutralized with 20% NaOH solution and diluted with diethyl ether. The two phases are separated and the organic layer washed with brine and water. The organic layer is dried over anhydrous sodium sulfate, filtered, and concentrated. Chromatography gives purified 5,5,5-trifluoro-2-[6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-pentanal (3.6 g, 10 mmol) 79% yield.

後処理

  1. temperatureheated
  2. temperatureto reflux under nitrogen
  3. temperatureto cool upon completion
  4. customThe two phases are separated
  5. washthe organic layer washed with brine and water
  6. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customChromatography gives

出典と根拠

ORDレコード
ord-59c285660d7e4f79acbc03d30a922e5b
出典データセット
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07989457B2

反応ノート

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