Diazald → trans-2-(3,4-Dimethoxy-5-nitrophenyl)-4-(3,4,5-trimethoxyphenyl)-1,3-dithiolane

HRID 1684034Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1684034
[CH3:1]C1C=CC(S(N(N=O)C)(=O)=O)=CC=1.[OH-].[K+].[N+](=C)=[N-].CCOCC.[OH:25][C:26]1[C:31]([N+:32]([O-:34])=[O:33])=[CH:30][C:29]([C@H:35]2[S:39][C@H:38]([C:40]3[CH:45]=[C:44]([O:46][CH3:47])[C:43]([O:48][CH3:49])=[C:42]([O:50][CH3:51])[CH:41]=3)[CH2:37][S:36]2)=[CH:28][C:27]=1[O:52][CH3:53]>C(OCC)C.C(Cl)(Cl)Cl.CO>[CH3:53][O:52][C:27]1[CH:28]=[C:29]([C@H:35]2[S:39][C@H:38]([C:40]3[CH:41]=[C:42]([O:50][CH3:51])[C:43]([O:48][CH3:49])=[C:44]([O:46][CH3:47])[CH:45]=3)[CH2:37][S:36]2)[CH:30]=[C:31]([N+:32]([O-:34])=[O:33])[C:26]=1[O:25][CH3:1]

Komponenten

8

Edukt 4

HCID 6628Diazald2×HCID 14797Potassium HydroxideHCID 21186548Diazomethane diethyletherHCID 86749583trans-2-(4-Hydroxy-3-methoxy-5-nitrophenyl)-4-(3,4,5-trimethoxyphenyl)-1,3-dithiolane

Produkt 1

HCID 86750974trans-2-(3,4-Dimethoxy-5-nitrophenyl)-4-(3,4,5-trimethoxyphenyl)-1,3-dithiolane

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

Using the Aldrich diazald kit, diazald (13.0 g, 60.7 mmole) predissolved in 100 ml diethyl ether was added dropwise to an aqueous potassium hydroxide solution (ethanol, 27 ml; H2O, 21 ml; and potassium hydroxide, 13.3 g) at 65° C. The diazomethane/ether distillate was added at 0° C. to a solution of trans-2-(4-hydroxy-3-methoxy-5-nitrophenyl)-4-(3,4,5-trimethoxyphenyl)-1,3-dithiolane (1) (FIG. 20) predissolved in 25 ml chloroform and 50 ml methanol. The reaction was stirred to completely homogenize the solution and was then allowed to stand at room temperature under an argon atmosphere for 5 hours. The solvent was removed in vacuo and the remaining oil was dissolved in 10 ml diethyl ether. The product crystallized out of the ether solution to yield 3.285 g (98%) of light yellow crystals.

Aufarbeitung

  1. stirringto completely homogenize the solution
  2. customThe solvent was removed in vacuo
  3. dissolutionthe remaining oil was dissolved in 10 ml diethyl ether
  4. customThe product crystallized out of the ether solution
  5. customto yield 3.285 g (98%) of light yellow crystals

Quellen und Nachweise

ORD-Eintrag
ord-fe6de001001b4613ba11469b748f56f4
Quelldatensatz
uspto-grants-1997_06
Patentnummer
US05639782

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