Tetrahydrofuran → p-(1-Hydroxyethyl)phenyl 2-thienyl ketone

HRID 461735

反応式

HRID 461735 の反応式
[Mg].Br[C:3]1[CH:17]=[CH:16][C:6]([CH:7]([CH3:15])[O:8]C2CCCCO2)=[CH:5][CH:4]=1.[S:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[C:23]#N.[Cl-].[NH4+].[O:27]1CCCC1>>[S:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[C:23]([C:3]1[CH:4]=[CH:5][C:6]([CH:7]([OH:8])[CH3:15])=[CH:16][CH:17]=1)=[O:27]

参加物

6

反応物 5

HCID 8028Tetrahydrofuran2 回HCID 25517Ammonium ChlorideHCID 660872-ThiophenecarbonitrileHCID 5462224MagnesiumHCID 112198612-(p-Bromo-alpha-methylbenzyloxy)tetrahydropyran

生成物 1

HCID 12232927p-(1-Hydroxyethyl)phenyl 2-thienyl ketone

実験手順

A Grignard-complex is formed starting from 7.2 parts of magnesium and 93.9 parts of 2-(p-bromo-α-methylbenzyloxy)tetrahydropyran in 200 parts of dry tetrahydrofuran. To this stirring and refluxing complex is added dropwise a solution of 32.7 parts of 2-thiophenecarbonitrile in 70 parts of dry tetrahydrofuran and stirring at reflux is continued for 4 hours. The reaction mixture is stirred overnight at room temperature. After cooling, it is decomposed with 150 parts of a saturated ammonium chloride solution at a temperature of about 15° C. The whole is poured onto water and extracted with ether. The organic phase is washed four times with water, dried, filtered and upon acidification of the filtrate with 2-propanol, previously saturated with gaseous hydrogen chloride, an oil is separated. The ether is decanted and the oil is triturated twice in ether. The latter is decanted each time and the oily product is dissolved in water. Concentrated hydrochloric acid solution is added (150 parts) and the whole is stirred with activated charcoal. The latter is filtered off and the filtrate is boiled for 10 minutes and extracted with ether. The combined extracts are washed with water, dried, filtered and evaporated, yielding p-(1-hydroxyethyl)phenyl 2-thienyl ketone, as an oily residue.

後処理

  1. customA Grignard-complex is formed
  2. temperatureTo this stirring and refluxing complex
  3. temperatureat reflux
  4. stirringThe reaction mixture is stirred overnight at room temperature
  5. temperatureAfter cooling
  6. additionThe whole is poured onto water
  7. extractionextracted with ether
  8. washThe organic phase is washed four times with water
  9. customdried
  10. filtrationfiltered and upon acidification of the filtrate with 2-propanol, previously saturated with gaseous hydrogen chloride
  11. customan oil is separated
  12. customThe ether is decanted
  13. customthe oil is triturated twice in ether
  14. customThe latter is decanted each time
  15. dissolutionthe oily product is dissolved in water
  16. additionConcentrated hydrochloric acid solution is added (150 parts)
  17. stirringthe whole is stirred with activated charcoal
  18. filtrationThe latter is filtered off
  19. waitthe filtrate is boiled for 10 minutes
  20. extractionextracted with ether
  21. washThe combined extracts are washed with water
  22. customdried
  23. filtrationfiltered
  24. customevaporated

出典と根拠

ORDレコード
ord-23c324d7a88b4185a9f0e62d91756111
出典データセット
uspto-grants-1977_12
特許番号
US04064132

関連ノート

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