Ethanol → Fenoprofen

HRID 1277761

反応式

HRID 1277761 の反応式
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

参加物

6

反応物 3

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

生成物 1

HCID 3342Fenoprofen収率 97%

試薬・触媒・溶媒 2

HCID 6386tert-Butanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-0da7657d2b4043b2b7734a3314e7d90a
出典データセット
uspto-grants-1981_07
特許番号
US04278802

関連ノート

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