Tetrahydrofuran → HCID 21391792, 화합물

HRID 1439557

반응식

HRID 1439557 반응식
[Mg].Br[C:3]1[CH:16]=[CH:15][C:6]([CH2:7][O:8]C2CCCCO2)=[CH:5][CH:4]=1.[S:17]1[CH:21]=[CH:20][CH:19]=[C:18]1[C:22]#N.[Cl-].[NH4+].[O:26]1CCCC1>>[S:17]1[CH:21]=[CH:20][CH:19]=[C:18]1[C:22]([C:3]1[CH:4]=[CH:5][C:6]([CH2:7][OH:8])=[CH:15][CH:16]=1)=[O:26]

참가 물질

6

반응물 5

HCID 8028Tetrahydrofuran2회HCID 25517Ammonium ChlorideHCID 660872-ThiophenecarbonitrileHCID 5981682-[(4-Bromophenyl)methoxy]oxaneHCID 5462224Magnesium

생성물 1

HCID 21391792HCID 21391792, 화합물

실험 절차

To a stirred and refluxing Grignard-complex, previously prepared starting from 7.2 parts of magnesium and 81.4 parts of 2-(p-bromobenzyloxy)tetrahydropyran in 200 parts of dry tetrahydrofuran, is added dropwise a solution of 32.7 parts of 2-thiophenecarbonitrile in 70 parts of dry tetrahydrofuran (exothermic reaction: reflux temperature is maintained). Upon completion, stirring at reflux is continued for 4 hours. The reaction mixture is cooled and decomposed with 150 parts of a saturated ammonium chloride solution at about 15° C. The whole is poured onto water and the product is extracted with ether. The organic layer is washed four times with water, dried, filtered and acidifed with gaseous hydrogen chloride: an oil is separated. The ether is decanted and the oily product is dissolved in 300 parts of water and 150 parts of concentrated hydrochloric acid solution. The solution is stirred with activated charcoal, filtered and the filtrate is stirred and refluxed for 10 minutes. The product is extracted with chloroform. The latter is washed with water, dried, filtered and evaporated. The residue is distilled, yielding α-hydroxy-p-tolyl 2-thienyl ketone; bp. 180°-190° C at 0.2 mm. pressure.

후처리

  1. temperaturerefluxing Grignard-complex
  2. custompreviously prepared
  3. stirringUpon completion, stirring
  4. temperatureat reflux
  5. temperatureThe reaction mixture is cooled
  6. additionThe whole is poured onto water
  7. extractionthe product is extracted with ether
  8. washThe organic layer is washed four times with water
  9. customdried
  10. filtrationfiltered
  11. customan oil is separated
  12. customThe ether is decanted
  13. dissolutionthe oily product is dissolved in 300 parts of water and 150 parts of concentrated hydrochloric acid solution
  14. stirringThe solution is stirred with activated charcoal
  15. filtrationfiltered
  16. stirringthe filtrate is stirred
  17. temperaturerefluxed for 10 minutes
  18. extractionThe product is extracted with chloroform
  19. washThe latter is washed with water
  20. customdried
  21. filtrationfiltered
  22. customevaporated
  23. distillationThe residue is distilled

출처 및 근거

ORD 기록
ord-1fbf318cc7064161a2c2bdbee133dd78
출처 데이터셋
uspto-grants-1977_11
특허 번호
US04060528

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