Hydrochloric Acid → Ethyl 3-(2-fluoro-4-biphenylyl)-2-butenoate

HRID 918150

반응식

HRID 918150 반응식
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:6]([F:16])[CH:5]=1)(=O)[CH3:2].[CH2:17]([O:19][C:20](=[O:23])[CH2:21]Br)[CH3:18].Cl.P(Cl)(Cl)Cl>CCOCC.O1CCCC1.C1C=CC=CC=1.[Zn].O>[F:16][C:6]1[CH:5]=[C:4]([C:1]([CH3:2])=[CH:21][C:20]([O:19][CH2:17][CH3:18])=[O:23])[CH:9]=[CH:8][C:7]=1[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

참가 물질

9

반응물 4

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 24387Phosphorus trichlorideHCID 64519181-(2-Fluoro(1,1'-biphenyl)-4-yl)ethan-1-one

생성물 1

HCID 53797937Ethyl 3-(2-fluoro-4-biphenylyl)-2-butenoate

시약·촉매·용매 4

HCID 23994Zinc촉매HCID 241Benzene용매HCID 962Water용매HCID 21868444Ether tetrahydrofuran용매

실험 절차

42.8 gm (0.20 mol) of 4-acetyl-2-fluoro-biphenyl were added in small portions, while stirring, to a Reformatsky reagent prepared from 57.5 gm (0.88 mol) of zinc and 73.5 gm (0.44 mol) of bromoacetic acid ethyl ester in 500 ml of absolute ether/tetrahydrofuran (1:1), and the resulting mixture was refluxed for one hour. Then, 1 liter of water was added, the reaction mixture was acidified with dilute hydrochloric acid, and the organic layer was separated, extracted again with water and dried over sodium sulfate. The raw 3-(2-fluoro-4-biphenylyl)-3-hydroxy-butyric acid ethyl ester remaining after the solvent had been distilled off was refluxed in 330 ml of benzene with 45 gm (0.293 mol) of phosphorus trichloride for 10 minutes, whereupon the solvent was distilled off, water was added to the residue and the precipitated oil was taken up in ether. The ether solution was washed with water and an aqueous 5% sodium bicarbonate solution until neutral, dried, filtered through charcoal, and the solvent was distilled out of the filtrate. The residue, raw 3-(2-fluoro-4-biphenylyl)-2-butenoic acid ethyl ester (39.9 gm, 70% of theory), was used as a starting compound without further purification.

후처리

  1. temperaturethe resulting mixture was refluxed for one hour
  2. customthe organic layer was separated
  3. extractionextracted again with water
  4. dry with materialdried over sodium sulfate
  5. distillationThe raw 3-(2-fluoro-4-biphenylyl)-3-hydroxy-butyric acid ethyl ester remaining after the solvent had been distilled off
  6. distillationwas distilled off
  7. additionwater was added to the residue
  8. washThe ether solution was washed with water
  9. dry with materialan aqueous 5% sodium bicarbonate solution until neutral, dried
  10. filtrationfiltered through charcoal
  11. distillationthe solvent was distilled out of the filtrate
  12. customThe residue, raw 3-(2-fluoro-4-biphenylyl)-2-butenoic acid ethyl ester (39.9 gm, 70% of theory), was used as a starting compound without further purification

출처 및 근거

ORD 기록
ord-cf92b890c2394305814db75427e6ccea
출처 데이터셋
uspto-grants-1976_07
특허 번호
US03969419

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