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Nitrogen → 4,4'-Tolan-dicarboxylic acid di-tert.-butyl ester

HRID 974209
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 974209
[C:1]([O:5][C:6](=[O:14])[C:7]1[CH:12]=[CH:11][C:10](Br)=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N#N.[C:36]([O:40][C:41](=[O:50])[C:42]1[CH:47]=[CH:46][C:45]([C:48]#[CH:49])=[CH:44][CH:43]=1)([CH3:39])([CH3:38])[CH3:37]>C(#N)C.[Cu]I.CCN(CC)CC>[C:1]([O:5][C:6]([C:7]1[CH:12]=[CH:11][C:10]([C:49]#[C:48][C:45]2[CH:46]=[CH:47][C:42]([C:41]([O:40][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:50])=[CH:43][CH:44]=2)=[CH:9][CH:8]=1)=[O:14])([CH3:4])([CH3:3])[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 947NitrogenHCID 11776TriphenylphosphineHCID 11334366Tert-butyl 4-bromobenzoateHCID 13965008Tert-butyl 4-ethynylbenzoate

Produkt 1

HCID 148475264,4'-Tolan-dicarboxylic acid di-tert.-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Katalysator
HCID 6342AcetonitrileLösungsmittel2×
HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

4-Bromo-benzoic acid tert.-butyl ester, 5.1 g of triphenylphosphine and 375 ml of NEt3 are introduced into 1 l of absolute acetonitrile under nitrogen and N2 is passed through the solution for 20 minutes. 10.5 g of (Pφ3)2PdCl2 and 1.5 g of copper(I)iodide are then added and 166.5 g of 4-ethinyl-benzoic acid tert.-butyl ester dissolved in 1 l of absolute acetonitrile are slowly added dropwise under reflux and the reaction mixture is stirred overnight. The resulting reaction mixture is then suction filtered after cooling, stirred up in water, again suction filtered, dissolved in CH2Cl2 and filtered after the addition of a small quantity of Tonsil, and the solvent is then evaporated off under vacuum. 225 g of 4,4'-Tolan-dicarboxylic acid-di-tert.-butyl ester are obtained.

Aufarbeitung

  1. additionare slowly added dropwise
  2. temperatureunder reflux
  3. customThe resulting reaction mixture
  4. filtrationsuction filtered
  5. temperatureafter cooling
  6. stirringstirred up in water
  7. filtrationagain suction filtered
  8. dissolutiondissolved in CH2Cl2
  9. filtrationfiltered
  10. additionafter the addition of a small quantity of Tonsil
  11. customthe solvent is then evaporated off under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-8b63aad949984d1eb9e3fd6260dad1c3
Quelldatensatz
uspto-grants-1991_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05068300

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