Dimethylformamide → HCID 58615402, 화합물

HRID 852994노트

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HRID 852994 반응식
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2[O:12][CH2:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.C([Li])CCC.CN(C)[CH:27]=[O:28]>C1COCC1.[Cl-].[NH4+]>[CH:14]1([CH2:13][O:12][C:5]2[C:4]3[C:9](=[CH:10][CH:11]=[C:2]([CH:27]=[O:28])[CH:3]=3)[N:8]=[CH:7][CH:6]=2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

참가 물질

6

반응물 3

HCID 6228DimethylformamideHCID 586153676-Bromo-4-cyclohexylmethoxy-quinolineHCID 178418339Butyllithium

생성물 1

HCID 58615402HCID 58615402, 화합물수율 48%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 25517Ammonium Chloride용매

실험 절차

To a solution of 6-bromo-4-cyclohexylmethoxy-quinoline (0.510 g, 1.59 mmol) in THF (10 mL) was added dropwise a 2.5M solution of n-butyllithium in hexanes (0.765 mL, 1.92 mmol, 1.2 equiv.) at −70° C. During the addition, the color of the solution was turned into red and this solution was stirred for 1 h at this temperature. Then, a solution of dimethylformamide (0.246 mL, 3.19 mmol) in THF (1 mL) was added dropwise. After addition, the mixture was allowed to warm to room temperature and stirred for 2 h. Then, the mixture was diluted with saturated ammonium chloride solution and the two layers were separated. The aqueous layer was extracted with ethyl acetate (3×150 mL). The combined organic extracts were washed with brine solution and dried over anhydrous magnesium sulfate. Filtration of the drying agent and removal of the solvent under the vacuum gave the crude residue which was purified by using a Biotage silica gel column chromatography to afford 0.205 g (48% yield) of 4-cyclohexylmethoxy-quinoline-6-carbaldehyde as a white solid: EI-HRMS m/e calcd for C17H19NO2 (M+) 269.3513, found 269.3511.

후처리

  1. additionDuring the addition
  2. additionAfter addition
  3. stirringstirred for 2 h
  4. customthe two layers were separated
  5. extractionThe aqueous layer was extracted with ethyl acetate (3×150 mL)
  6. washThe combined organic extracts were washed with brine solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationFiltration of the drying agent and removal of the solvent under the vacuum
  9. customgave the crude residue which
  10. customwas purified

출처 및 근거

ORD 기록
ord-a6c85ebe63f7402ca130200f336997fb
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07253285B2

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