p-Toluenesulfonic acid → HCID 27234258, 화합물

HRID 1077150

반응식

HRID 1077150 반응식
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]

참가 물질

7

반응물 4

HCID 6101p-Toluenesulfonic acidHCID 214854206-m-Acetoxyphenyl-1-diethylaminohexan-3-oneHCID 214855806-m-Acetoxyphenylhex-1-en-3-oneHCID 21485772HCID 21485772, 화합물

생성물 1

HCID 27234258HCID 27234258, 화합물

시약·촉매·용매 2

HCID 241Benzene용매HCID 3283Diethyl Ether용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ff41c2cd4a0240ac8b97c3e893e2ffde
출처 데이터셋
uspto-grants-1976_05
특허 번호
US03959322

연결된 노트

불러오는 중…