Ethyl Acetate → 1-phenyl-5-(2,4,5-trifluorophenyl)-1H-pyrazole-4-carbaldehyde

HRID 402760

반응식

HRID 402760 반응식
[C:1]1([N:7]2[C:11]([C:12]3[CH:17]=[C:16]([F:18])[C:15]([F:19])=[CH:14][C:13]=3[F:20])=[C:10]([C:21](OCC)=[O:22])[CH:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.CCOC(C)=O>C1COCC1.C(Cl)Cl>[C:1]1([N:7]2[C:11]([C:12]3[CH:17]=[C:16]([F:18])[C:15]([F:19])=[CH:14][C:13]=3[F:20])=[C:10]([CH:21]=[O:22])[CH:9]=[N:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 159087TriacetoxyperiodinaneHCID 21226445Aluminium lithium hydrideHCID 86685264ethyl 1-phenyl-5-(2,4,5-trifluorophenyl)-1H-pyrazole-4-carboxylate

생성물 1

HCID 866852651-phenyl-5-(2,4,5-trifluorophenyl)-1H-pyrazole-4-carbaldehyde

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
50 °C

실험 절차

To a solution of ethyl 1-phenyl-5-(2,4,5-trifluorophenyl)-1H-pyrazole-4-carboxylate (459 mg, 1.325 mmol) in THF (5 mL) was added LAH (1.988 mL, 1.988 mmol as a 1 M THF solution) at room temperature and the reaction was then heated at 50° C. for 2 hours. The reaction was quenched with addition of 0.2 mL of water, 0.2 mL of 0.5 N NaOH and then 0.2 mL of water. The suspension was diluted with ether and was filtered through celite. Upon removal of the volatiles, the crude residue was purified by flash chromatography to afford an oil. The oil was then dissolved in 5 mL of CH2Cl2 and Dess-Martin periodinane (233.8 mg, 0.768 mmol) was added. The suspension was stirred at room temperature for 16 hours. The mixture was poured into EtOAc and was washed with brine. The organic phase was dried with Na2SO4, filtered and concentrated. The crude residue was purified by flash chromatography using a gradient of ethyl acetate/hexanes to afford the title intermediate as white solid.

후처리

  1. customThe reaction was quenched with addition of 0.2 mL of water, 0.2 mL of 0.5 N NaOH
  2. additionThe suspension was diluted with ether
  3. filtrationwas filtered through celite
  4. customUpon removal of the volatiles
  5. customthe crude residue was purified by flash chromatography
  6. customto afford an oil
  7. washwas washed with brine
  8. dry with materialThe organic phase was dried with Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe crude residue was purified by flash chromatography

출처 및 근거

ORD 기록
ord-e874e09684ad430185186aa98612fc67
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08742110B2

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