p-Toluenesulfonic acid → HCID 27234258、化合物

HRID 1077150

反応式

HRID 1077150 の反応式
C(OC1C=C(CCCC(=O)[CH2:15][CH2:16][C:17]2([CH3:24])[C:21](=O)[CH2:20][CH2:19][C:18]2=[O:23])C=CC=1)(=O)C.C([O:29][C:30]1[CH:31]=[C:32]([CH2:36][CH2:37][CH2:38][C:39](=O)CCN(CC)CC)[CH:33]=[CH:34][CH:35]=1)(=O)C.C(OC1C=C(CCCC(=O)C=C)C=CC=1)(=O)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1.CCOCC>[CH3:24][C@:17]12[CH2:16][CH2:15][C:39]3[C:33]4[CH:34]=[CH:35][C:30]([OH:29])=[CH:31][C:32]=4[CH2:36][CH2:37][C:38]=3[C:21]1=[CH:20][CH2:19][C:18]2=[O:23]

参加物

7

反応物 4

HCID 6101p-Toluenesulfonic acidHCID 214854206-m-Acetoxyphenyl-1-diethylaminohexan-3-oneHCID 214855806-m-Acetoxyphenylhex-1-en-3-oneHCID 21485772HCID 21485772、化合物

生成物 1

HCID 27234258HCID 27234258、化合物

試薬・触媒・溶媒 2

HCID 241Benzene溶媒HCID 3283Diethyl Ether溶媒

実験手順

Reflux 2-(6-m-acetoxyphenyl-3-oxohexyl)-2-methylcyclopentane-1,3-dione (0.8 g, the product of Michael condensation of 2-methylcyclopentanedione and a mixture of 6-m-acetoxyphenyl-1-diethylaminohexan-3-one and 6-m-acetoxyphenylhex-1-en-3-one, and containing some of the corresponding free phenolic compound) in benzene (25 cc) with toluene-p-sulfonic acid (0.3 g) for 50 minutes. On cooling add ether (50 cc) and wash the mixture in turn with water, saturated aqueous potassium bicarbonate, and brine; dry over anhydrous magnesium sulfate. The residue after removal of solvent is a purple gum (0.6 g), part of which can be induced to crystallize. Dissolve a portion (0.45 g) of this gum in benzene and adsorb on an activated Fuller's earth (40 g); elute with benzene to obtain 13β-methyl-3-hydroxygona-1,3,5(10),8,14-pentaen-17-one, which one recrystallizes from diisopropyl ether, m.p. 225°-226°; ultraviolet absorption peak at 312.5 mμ (ε23,000); infrared absorption peaks at 2.99 μ, 5.81 μ, and 8.00μ.

後処理

  1. temperatureOn cooling
  2. washwash the mixture in turn with water, saturated aqueous potassium bicarbonate, and brine
  3. dry with materialdry over anhydrous magnesium sulfate
  4. customThe residue after removal of solvent
  5. customto crystallize
  6. dissolutionDissolve a portion (0.45 g) of this gum in benzene
  7. washelute with benzene

出典と根拠

ORDレコード
ord-ff41c2cd4a0240ac8b97c3e893e2ffde
出典データセット
uspto-grants-1976_05
特許番号
US03959322

関連ノート

読み込み中…