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

HRID 402760

反応式

HRID 402760 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
50 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e874e09684ad430185186aa98612fc67
出典データセット
uspto-grants-2014_06
特許番号
US08742110B2

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