Citric Acid → HCID 10609230、化合物

HRID 1683498ノート

反応式

HRID 1683498 の反応式
[C:1]([NH:4][C:5]1[CH:14]=[C:13]([F:15])[C:12]([F:16])=[C:11]2[C:6]=1[CH2:7][CH2:8][CH2:9][C:10]2=O)(=[O:3])[CH3:2].C(O)C.[BH4-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(Cl)(Cl)Cl>[C:1]([NH:4][C:5]1[CH:14]=[C:13]([F:15])[C:12]([F:16])=[C:11]2[C:6]=1[CH2:7][CH2:8][CH2:9][CH2:10]2)(=[O:3])[CH3:2]

参加物

6

反応物 4

HCID 311Citric AcidHCID 702EthanolHCID 4311764Sodium borohydrideHCID 224495485-Acetylamino-7,8-difluoro-1-tetralone

生成物 1

HCID 10609230HCID 10609230、化合物

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

The compound obtained in (5) above (1 gm) was dissolved into 20 ml of ethanol. To the solution was added 166 mg of sodium borohydride while stirring at room temperature. After stirring for 20 minutes, chloroform and 10% citric acid were added to the reaction mixture. The chloroform layer was extracted and concentrated. To the concentrate were added 20 ml of toluene and a small amount of p-TsOH, followed by heating under reflux for 1 hour. Upon addition of 100 ml of ethyl acetate, the reaction product was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated and the residue was dissolved into a mixed solvent of 20 ml of ethanol, 20 ml of dioxane, and 0.2 ml of acetic acid. The mixture was catalytically hydrogenated with the addition of 200 mg of platinum oxide. The catalyst was removed, the filtrate was concentrated, and ether was added to the concentrate. 0.8 gm of the title compound was obtained by collecting the precipitate by filtration.

後処理

  1. stirringAfter stirring for 20 minutes
  2. extractionThe chloroform layer was extracted
  3. concentrationconcentrated
  4. additionTo the concentrate were added 20 ml of toluene
  5. temperatureby heating
  6. temperatureunder reflux for 1 hour
  7. additionUpon addition of 100 ml of ethyl acetate
  8. washthe reaction product was washed with saturated brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. customThe solvent was evaporated
  11. dissolutionthe residue was dissolved into a mixed solvent of 20 ml of ethanol, 20 ml of dioxane, and 0.2 ml of acetic acid
  12. additionThe mixture was catalytically hydrogenated with the addition of 200 mg of platinum oxide
  13. customThe catalyst was removed
  14. concentrationthe filtrate was concentrated
  15. additionether was added to the concentrate

出典と根拠

ORDレコード
ord-d37305146b12459890cc76892ec0e47e
出典データセット
uspto-grants-1997_06
特許番号
US05637770

反応ノート

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