Ethanol → Fenoprofen

HRID 1277761

반응식

HRID 1277761 반응식
CS[C:3]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:9]=1)([CH3:7])[C:4]([OH:6])=[O:5].[Na].C(O)C>C(O)(C)(C)C.O1CCCC1>[O:14]([C:10]1[CH:9]=[C:8]([CH:3]([CH3:7])[C:4]([OH:6])=[O:5])[CH:13]=[CH:12][CH:11]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

참가 물질

6

반응물 3

HCID 702EthanolHCID 5360545SodiumHCID 12917672alpha-Methylthio-alpha-(m-phenoxyphenyl)propionic acid

생성물 1

HCID 3342Fenoprofen수율 97%

시약·촉매·용매 2

HCID 6386tert-Butanol용매HCID 8028Tetrahydrofuran용매

실험 절차

α-Methylthio-α-(m-phenoxyphenyl)propionic acid (288 mg) was dissolved in a mixture of 1 ml of t-butanol and 4 ml of tetrahydrofuran, and 100 mg of metallic sodium was added. The mixture was stirred at room temperature for 10 minutes. The mixture was heated under reflux for an additional 1.5 hours with stirring. After cooling, a small amount of ethanol was added to consume the unreacted metallic sodium completely. Water (20 ml) was added, and the pH of the mixture was adjusted to 1 with conc. hydrochloric acid. The mixture was extracted three times with 27 ml of diethyl ether. The extract was washed twice with 20 ml of water, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and chromatographed on a silica gel column using methylene chloride as an eluent to afford 234 mg of α-(m-phenoxyphenyl)propionic acid in a yield of 97%.

후처리

  1. additionwas added
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for an additional 1.5 hours
  4. stirringwith stirring
  5. temperatureAfter cooling
  6. customto consume the unreacted metallic sodium completely
  7. additionWater (20 ml) was added
  8. extractionThe mixture was extracted three times with 27 ml of diethyl ether
  9. washThe extract was washed twice with 20 ml of water
  10. dry with materialdried over anhydrous magnesium sulfate
  11. concentrationconcentrated under reduced pressure
  12. customchromatographed on a silica gel column

출처 및 근거

ORD 기록
ord-0da7657d2b4043b2b7734a3314e7d90a
출처 데이터셋
uspto-grants-1981_07
특허 번호
US04278802

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