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

HRID 33999

반응식

HRID 33999 반응식
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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 3283Diethyl Ether용매HCID 8058Hexane용매HCID 8857Ethyl Acetate용매

반응 조건

온도
-20 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-301457584e034ef78be9b798feba0750
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07429609B2

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