Iodine → alpha-Methyl-alpha-(4-phenoxyphenyl)-3-pyridinemethanol

HRID 866430

反応式

HRID 866430 の反応式
[CH:1]1[CH:6]=[CH:5][C:4]([O:7][C:8]2[CH:13]=[CH:12][C:11](Br)=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.[Mg].II.[C:18]([C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1)(=[O:20])[CH3:19].[Cl-].[NH4+]>O1CCCC1>[O:7]([C:8]1[CH:13]=[CH:12][C:11]([C:18]([C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)([OH:20])[CH3:19])=[CH:10][CH:9]=1)[C:4]1[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1

参加物

7

反応物 5

HCID 807IodineHCID 75654-Bromodiphenyl EtherHCID 95893-AcetylpyridineHCID 25517Ammonium ChlorideHCID 5462224Magnesium

生成物 1

HCID 22768039alpha-Methyl-alpha-(4-phenoxyphenyl)-3-pyridinemethanol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

25 ml. of a solution of 25.0 g. 4-bromodiphenylether in 75 ml. tetrahydrofuran is added to 2.5 g. magnesium and, admixed with a small crystal of iodine to initiate the Grignard reaction. Thereafter, the remainder of the solution is added dropwise to maintain gentle reflux. The Grignard solution is then refluxed for 0.5 hours, cooled to 5°-10° and to it is added dropwise 12.1 g. of 3-acetylpyridine. The reaction mixture is then stirred at room temperature for 16 hours, decomposed with saturated aqueous ammonium chloride solution and extracted with ether. The ether extracts are combined and after drying over anhydrous sodium sulfate, filtered and evaporated i.v. to dryness. From the residue is crystallized from pentane/ether, 1-(p-phenoxyphenyl)-1-(3-pyridyl)-ethan-1-ol, m.p. 130°-132°.

後処理

  1. customthe Grignard reaction
  2. additionThereafter, the remainder of the solution is added dropwise
  3. temperatureto maintain gentle reflux
  4. temperatureThe Grignard solution is then refluxed for 0.5 hours
  5. temperaturecooled to 5°-10° and to it
  6. additionis added dropwise 12.1 g
  7. extractionextracted with ether
  8. dry with materialafter drying over anhydrous sodium sulfate
  9. filtrationfiltered
  10. customevaporated i.v
  11. customFrom the residue is crystallized from pentane/ether, 1-(p-phenoxyphenyl)-1-(3-pyridyl)-ethan-1-ol, m.p. 130°-132°

出典と根拠

ORDレコード
ord-9039b3d8daf742aaa5828c968021967a
出典データセット
uspto-grants-1978_07
特許番号
US04098908

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