Ammonium Chloride → (3-Fluorophenyl)-(3-fluoropyridin-2-yl)-methanol

HRID 33999

反応式

HRID 33999 の反応式
C([Li])CCC.[F:6][C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1.[F:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH:17]=[O:18].[Cl-].[NH4+]>C(OCC)C.CCCCCC.C(OCC)(=O)C>[F:13][C:14]1[CH:15]=[C:16]([CH:17]([C:8]2[C:7]([F:6])=[CH:12][CH:11]=[CH:10][N:9]=2)[OH:18])[CH:19]=[CH:20][CH:21]=1

参加物

8

反応物 4

HCID 25517Ammonium ChlorideHCID 677943-FluoropyridineHCID 680093-FluorobenzaldehydeHCID 178418339Butyllithium

生成物 1

HCID 23070231(3-Fluorophenyl)-(3-fluoropyridin-2-yl)-methanol

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
-20 °C

実験手順

Under nitrogen atmosphere, a solution of 9.75 g of diazabicyclo[2.2.0]octane in 150 mL of dehydrated diethyl ether was cooled to −40° C., added with 56 mL of 1.56 M n-butyllithium in hexane, and stirred at −20° C. for 1 hour. The solution was cooled to-60° C., added dropwise with 6.9 mL of 3-fluoropyridine, stirred at −60° C. for 1 hour, and added with 9.2 mL of 3-fluorobenzaldehyde. After stirring for 1 hour, aqueous ammonium chloride and ethyl acetate were successively added, and the mixture was recovered to room temperature. The organic layer was extracted, washed with water, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, and the resulting crude product was purified and separated by silica gel column chromatography (ethyl acetate:hexane=1:4), to give 12.6 g of the title compound as colorless needle crystals.

後処理

  1. temperatureThe solution was cooled to-60° C.
  2. stirringstirred at −60° C. for 1 hour
  3. stirringAfter stirring for 1 hour
  4. customthe mixture was recovered to room temperature
  5. extractionThe organic layer was extracted
  6. washwashed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated
  9. customthe resulting crude product was purified
  10. customseparated by silica gel column chromatography (ethyl acetate:hexane=1:4)

出典と根拠

ORDレコード
ord-301457584e034ef78be9b798feba0750
出典データセット
uspto-grants-2008_09
特許番号
US07429609B2

関連ノート

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