Diisopropylamine → 4-Fluoro-3-formyl-2-methoxybenzonitrile

HRID 34015

반응식

HRID 34015 반응식
C(NC(C)C)(C)C.C([Li])CCC.[F:13][C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[C:16]([O:22][CH3:23])[CH:15]=1.[CH:24](N1CCCCC1)=[O:25]>O1CCCC1.CCCCCC.O.C(O)(=O)C>[F:13][C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[C:16]([O:22][CH3:23])[C:15]=1[CH:24]=[O:25]

참가 물질

9

반응물 4

HCID 7912DiisopropylamineHCID 174291-PiperidinecarboxaldehydeHCID 27833294-Fluoro-2-methoxybenzonitrileHCID 178418339Butyllithium

생성물 1

HCID 230702244-Fluoro-3-formyl-2-methoxybenzonitrile수율 37.2%

시약·촉매·용매 4

HCID 176Acetic Acid용매HCID 962Water용매HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

실험 절차

Under nitrogen atmosphere and at −78° C., to a solution of 10.7 g of N,N-diisopropylamine in 150 mL of tetrahydrofuran was added 40 mL of 2.66 M n-butyllithium in n-hexane, stirred at this temperature for 1 hour and 15 minutes, and added dropwise with a solution of 14.5 g of 4-fluoro-2-methoxybenzonitrile obtained by Production example 95 in 50 mL of tetrahydrofuran. After stirring at this temperature for 2 hours, 11.94 g of N-formylpiperidine was added. After stirring at this temperature for 40 minutes, the solution was added with 20 mL of acetic acid at this temperature, added with water at room temperature, and extracted three times with diethyl ether. The organic layer was washed successively with 0.2N hydrochloric acid, water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the crude product was purified and separated by silica gel column chromatography, to afford 6.4 g of the title compound 6.4 g as pale yellow crystals.

후처리

  1. stirringAfter stirring at this temperature for 2 hours
  2. stirringAfter stirring at this temperature for 40 minutes
  3. extractionextracted three times with diethyl ether
  4. washThe organic layer was washed successively with 0.2N hydrochloric acid, water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated
  7. customthe crude product was purified
  8. customseparated by silica gel column chromatography

출처 및 근거

ORD 기록
ord-9061043c4833450aa11be9ccb3507016
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07429609B2

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