3-(4-Hydroxyphenyl)propionic acid → 4-[2-(4,5-Diphenyl-2-oxazolyl)ethyl]phenol

HRID 257640

반응식

HRID 257640 반응식
[Na].[OH:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([OH:13])=O)=[CH:5][CH:4]=1.Br[CH:15]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=O.C([O-])(=O)C.[NH4+:34]>C(O)C.OS(O)(=O)=O.C(O)(=O)C.O>[C:18]1([C:16]2[N:34]=[C:11]([CH2:10][CH2:9][C:6]3[CH:5]=[CH:4][C:3]([OH:2])=[CH:8][CH:7]=3)[O:13][C:15]=2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

참가 물질

9

반응물 4

HCID 103943-(4-Hydroxyphenyl)propionic acidHCID 1026302-Bromo-1,2-diphenylethan-1-oneHCID 517165Ammonium AcetateHCID 5360545Sodium

생성물 1

HCID 197836234-[2-(4,5-Diphenyl-2-oxazolyl)ethyl]phenol수율 65.1%

시약·촉매·용매 4

HCID 1118Sulfuric Acid촉매HCID 176Acetic Acid용매HCID 702Ethanol용매HCID 962Water용매

실험 절차

Sodium metal (1.00 g, 43 mg atom) was dissolved in ethanol (125 mL) and 3-(4-hydroxyphenyl)propionic acid (6.04 g, 36 mmol) added to give a white precipitate. The mixture was warmed briefly with stirring and concentrated H2SO4 (3 drops) added followed by 2-bromo-2-phenylacetophenone (1.00 g, 36 mmol). The mixture was heated at reflux for 2 hours, cooled, concentrated and diluted with water. The mixture was extracted with CH2Cl2, the combined extracts dried over sodium sulfate and concentrated to give an oil which was dissolved in acetic acid (250 mL). Ammonium acetate (14.00 g, 180 mmol) was added and the mixture heated to reflux. After 100 minutes, the solution was cooled, diluted with water and extracted with CH2Cl2. The combined extracts were dried over sodium sulfate and the solvent evaporated to leave a solid that was triturated with a mixture of hexanes and diethyl ether and filtered to give 4-[2 -(4,5-diphenyl-2-oxazolyl)ethyl]phenol (8.00 g, 64%). An analytical sample was prepared by recrystallizing 1.5 g from a mixture of hexanes and CH2Cl2 to give 1.20 g of pure material, m.p. 142°-144° C.

후처리

  1. customto give a white precipitate
  2. temperatureThe mixture was warmed briefly
  3. temperatureThe mixture was heated
  4. temperatureat reflux for 2 hours
  5. temperaturecooled
  6. concentrationconcentrated
  7. additiondiluted with water
  8. extractionThe mixture was extracted with CH2Cl2
  9. dry with materialthe combined extracts dried over sodium sulfate
  10. concentrationconcentrated
  11. customto give an oil which
  12. temperaturethe mixture heated to reflux
  13. temperaturethe solution was cooled
  14. extractionextracted with CH2Cl2
  15. dry with materialThe combined extracts were dried over sodium sulfate
  16. customthe solvent evaporated
  17. customto leave a solid
  18. customthat was triturated with a mixture of hexanes and diethyl ether
  19. filtrationfiltered

출처 및 근거

ORD 기록
ord-5ed5493abe86493caa1b6c377111fbeb
출처 데이터셋
uspto-grants-1993_11
특허 번호
US05262540

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