Diethyl Malonate → HCID 22262962, Verbindung

HRID 489822

Reaktionsgleichung

Reaktionsgleichung von HRID 489822
C[C@H]1C[O:29][C@@:5]2([O:9][C@H:8]3C[C@H]4[C@@H]5CC=C6C[C@@H](O)CC[C@]6(C)[C@H]5CC[C@]4(C)[C@H:7]3[C@@H]2C)[CH2:4]C1.C(OCC)(=O)C[C:33](OCC)=[O:34].[CH2:42]([C:44]1([CH2:48][OH:49])[CH2:47][O:46][CH2:45]1)[CH3:43].C([Sn](=O)CCCC)CCC>>[CH2:42]([C:44]12[CH2:47][O:46][C:45]([CH2:4][C:5]([O:9][CH2:8][CH3:7])=[O:29])([O:49][CH2:48]1)[O:34][CH2:33]2)[CH3:43]

Komponenten

5

Edukt 4

HCID 7761Diethyl MalonateHCID 61221Dibutyltin oxideHCID 76444Oxt-101HCID 99474Diosgenin

Produkt 1

HCID 22262962HCID 22262962, Verbindung

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

Into a 4 l three necked flask equipped with a stirrer, a distilling column, a nitrogen in- and outlet, a heating jacket, a thermocouple, and a vacuum pump were charged 1920 g of diethyl malonate (12 moles), 464 g of 3-ethyl-3-hydroxymethyl oxetane (4 moles), and 2,5 g of dibutyl tin oxide. The reaction mixture was heated to 140° C. upon which temperature the ethanol distillation began. The reaction temperature was gradually increased to 200° C. during 6 hours. During this time 171 g of ethanol were collected as distillate. The temperature was lowered to 100° C. and the pressure was lowered to 29 mbar by application of vacuum. The excess diethylmalonate was distilled off. The pressure was further lowered to 0.03 mbar and the temperature was gradually increased to 156° C. Three fractions of distillate were collected. The third fraction (100–104° C./0.03 mbar) consisted of 379 g, which according to GC analysis contained 75% of 4-ethyl-1-(ethoxycarbonylmethyl)-2,6,7-trioxabicyclo[2.2.2]octane having the following structure

Aufarbeitung

  1. distillationthe ethanol distillation
  2. temperatureThe reaction temperature was gradually increased to 200° C. during 6 hours
  3. distillationDuring this time 171 g of ethanol were collected as distillate
  4. customwas lowered to 100° C.
  5. distillationThe excess diethylmalonate was distilled off
  6. temperaturethe temperature was gradually increased to 156° C
  7. distillationThree fractions of distillate were collected
  8. customThe third fraction (100–104° C./0.03 mbar)

Quellen und Nachweise

ORD-Eintrag
ord-3acc812c26734cadabbdc462384f148e
Quelldatensatz
uspto-grants-2005_12
Patentnummer
US06979719B1

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