Ethylene Glycol → 13beta-Ethyl-3-methoxy-6-methyl-17,17-ethylenedioxygona-1,3,5(10),8,14-pentaene

HRID 1415045ノート

反応式

HRID 1415045 の反応式
[CH2:1]([C:3]1([CH2:10][CH2:11][C:12](=O)[CH2:13][CH2:14][CH:15]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19](OC)[CH:18]=2)[CH3:16])[C:7](=O)[CH2:6][CH2:5][C:4]1=O)[CH3:2].[C:26]1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:37]([OH:40])[CH2:38][OH:39].[OH2:41]>C1C=CC=CC=1>[CH2:1]([C@:3]12[CH2:10][CH2:11][C:12]3[C:18]4[CH:19]=[CH:20][C:21]([O:41][CH3:26])=[CH:22][C:17]=4[CH:15]([CH3:16])[CH2:14][C:13]=3[C:7]1=[CH:6][CH2:5][C:4]12[O:40][CH2:37][CH2:38][O:39]1)[CH3:2]

参加物

6

反応物 4

HCID 174Ethylene GlycolHCID 962Water2 回HCID 6101p-Toluenesulfonic acidHCID 214854092-Ethyl-2-(6-m-methoxyphenyl-6-methyl-3-oxohexyl)-1,3-cyclopentanedione

生成物 1

HCID 6814525013beta-Ethyl-3-methoxy-6-methyl-17,17-ethylenedioxygona-1,3,5(10),8,14-pentaene

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

Dissolve 2-ethyl-2-(6-m-methoxyphenyl-6-methyl-3-oxohexyl)-1,3-cyclopentanedione (39.7 g) in benzene (500 ml) and reflux with p-toluenesulfonic acid in water (11.0 g). Remove 2 moles of water, add ethyleneglycol (50 ml) and reflux the solution overnight (16 hours). After working up by the usual procedure, filter repeatedly through Florex in hexane. Recrystallize from ethanol to obtain dl-13β-ethyl-3-methoxy-6-methyl-17,17-ethylenedioxygona-1,3,5-(10),8,14-pentaene (16.8 g), m.p. 120°-122°; ultraviolet absorption peak at 312 mμ, no infrared absorption in the ketone region.

後処理

  1. temperaturereflux the solution overnight (16 hours)
  2. filtrationfilter repeatedly through Florex in hexane
  3. customRecrystallize from ethanol

出典と根拠

ORDレコード
ord-10975977f31349ba8cce3a154ea5eee0
出典データセット
uspto-grants-1977_01
特許番号
US04002746

反応ノート

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