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

HRID 1415045노트

반응식

HRID 1415045 반응식
[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]

참가 물질

6

반응물 4

HCID 174Ethylene GlycolHCID 962Water2회HCID 6101p-Toluenesulfonic acidHCID 214854092-Ethyl-2-(6-m-methoxyphenyl-6-methyl-3-oxohexyl)-1,3-cyclopentanedione

생성물 1

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

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-10975977f31349ba8cce3a154ea5eee0
출처 데이터셋
uspto-grants-1977_01
특허 번호
US04002746

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