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Carbon Dioxide → 3-Ethyl 5-hydrogen 2,6-bis(trifluoromethyl)-4-chloro-3,5-pyridinedicarboxylate

HRID 255411
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 255411
[Li+].CC([N-]C(C)C)C.[F:9][C:10]([F:28])([F:27])[C:11]1[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:15]([Cl:22])[CH:14]=[C:13]([C:23]([F:26])([F:25])[F:24])[N:12]=1.[C:29](=[O:31])=[O:30].Cl>COCCOC.O>[F:28][C:10]([F:9])([F:27])[C:11]1[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:15]([Cl:22])[C:14]([C:29]([OH:31])=[O:30])=[C:13]([C:23]([F:24])([F:25])[F:26])[N:12]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 2724682Lithium diisopropylamideHCID 138828774-Chloro-2,6-bis-trifluoromethyl-nicotinic acid ethyl ester

Produkt 1

HCID 140137833-Ethyl 5-hydrogen 2,6-bis(trifluoromethyl)-4-chloro-3,5-pyridinedicarboxylateAusbeute 37,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a -78° C. solution of LDA (0.128 mol) in 85 ml of DME was added a solution of 18.28 g (0.057 mol) of product of Example 9 in 20 ml of DME. The reaction mixture was stirred at -78° C. for 1 hour. To the above solution was added excess of dry ice. After stirring at -78° C. the reaction mixture was warmed to room temperature in 1 hour and poured into 250 ml of water containing 50 ml of concentrated HCl. The oil precipitate was extracted into ether. The ether extract was extracted with saturated NaHCO3. The basic extract was made acidic with concentrated HCl. The oil precipitate was extracted into ether. The ether solution was dried (MgSO4) and concentrated in vacuo to give 7.81 g (37.6%) of product as a solid; mp 113°-115° C.

Aufarbeitung

  1. stirringAfter stirring at -78° C. the reaction mixture
  2. temperaturewas warmed to room temperature in 1 hour
  3. extractionThe oil precipitate was extracted into ether
  4. extractionThe ether extract
  5. extractionwas extracted with saturated NaHCO3
  6. extractionThe basic extract
  7. extractionThe oil precipitate was extracted into ether
  8. dry with materialThe ether solution was dried (MgSO4)
  9. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-66c25f1dc98e4f5f80fa1188859f4ce9
Quelldatensatz
uspto-grants-1987_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04698093

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