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Potassium Carbonate → 1,2-dibenzyl 1-tert.butyl 4-methyl-1-(5-phenyl-pent-2-en-1-yl)-1,1,2(R)-pentanetricarboxylate

HRID 1464363
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1464363
[CH:1]([CH2:3][C:4]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])([C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21])[C@H:5]([C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])[CH2:6][CH:7]([CH3:9])[CH3:8])=O.C(=O)([O-])[O-].[K+].[K+].[Br-].[C:44]1([CH2:50][CH2:51][CH2:52][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>O1CCCC1>[CH3:9][CH:7]([CH3:8])[CH2:6][C@@H:5]([C:10]([O:12][CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[O:11])[C:4]([CH2:3][CH:1]=[CH:52][CH2:51][CH2:50][C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1)([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21]
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Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 109286473-Phenylpropyl triphenylphosphonium bromideHCID 867477791,2-dibenzyl 1-tert.butyl 1-(formylmethyl)-4-methyl-1,1,2(R)-pentanetricarboxylate

Produkt 1

HCID 678264681,2-dibenzyl 1-tert.butyl 4-methyl-1-(5-phenyl-pent-2-en-1-yl)-1,1,2(R)-pentanetricarboxylateAusbeute 66,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 0.496 g of 1,2-dibenzyl 1-tert.butyl 1-(formylmethyl)-4-methyl-1,1,2(R)-pentane tricarboxylate, 0.176 g of potassium carbonate and 0.576 g of 3-phenylpropyltriphenylphosphonium bromide in 8 ml of dry tetrahydrofuran was heated at reflux under a nitrogen atmosphere for 3 days. The solvent was removed by evaporation and stirred with diethyl acetate. The solids which separated were filtered off and the filtrate was evaporated. The residue was purified by flash chromatography on silica gel using hexane/ethyl acetate (6:1) for the elution. There was obtained 0.397 g of 1,2-dibenzyl 1-tert.butyl 4-methyl-1-(5-phenyl-pent-2-en-1-yl)-1,1,2(R)-pentanetricarboxylate in the form of a colorless oil.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux under a nitrogen atmosphere for 3 days
  3. customThe solvent was removed by evaporation
  4. customThe solids which separated
  5. filtrationwere filtered off
  6. customthe filtrate was evaporated
  7. customThe residue was purified by flash chromatography on silica gel
  8. washfor the elution

Quellen und Nachweise

ORD-Eintrag
ord-5c9379443acd4f52a3f6cb16c13df896
Quelldatensatz
uspto-grants-1994_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05304549

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