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

HRID 1649656
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1649656
[Li+].CC([N-]C(C)C)C.[F:9][C:10]([F:30])([F:29])[C:11]1[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:15]([O:22][CH2:23][CH3:24])[CH:14]=[C:13]([C:25]([F:28])([F:27])[F:26])[N:12]=1.[C:31](=[O:33])=[O:32]>COCCOC>[F:30][C:10]([F:29])([F:9])[C:11]1[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:15]([O:22][CH2:23][CH3:24])[C:14]([C:31]([OH:33])=[O:32])=[C:13]([C:25]([F:28])([F:27])[F:26])[N:12]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 280Carbon DioxideHCID 2724682Lithium diisopropylamide2×HCID 13882869Ethyl 2,6-bis(trifluoromethyl)-4-ethoxy-3-pyridinecarboxylate2×

Produkt 1

HCID 140137533-Ethyl 5-hydrogen 2,6-bis(trifluoromethyl)-4-ethoxy-3,5-pyridinedicarboxylateAusbeute 52,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8071
1,2-Dimethoxyethane
Lösungsmittel
2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

This material was prepared in 52.7% yield from 0.06 mol of LDA and 0.024 mol of product of Example 6 according to the following general procedure as a beige solid, mp 115°-117° C. To a -78° C. solution of 2.5 eq (0.06 mol) of LDA in DME was added a solution of 1 eq (0.024 mol) of starting material, the monocarboxylate product (Example 6) in dry DME. The resulting dark colored solution was stirred for 30 minutes at -78° C. To the above solution was added excess of dry ice. The reaction mixture was stirred at -78° C. for 15 minutes and warmed to room temperature in 1 hour. The reaction mixture was poured into ice water (100 ml) and extracted with ether. The aqueous layer was made acidic. The oil precipitate was extracted with ether. The ether extract was dried (MgSO4) and concentrated in vacuo to give the desired product.

Aufarbeitung

  1. stirringThe reaction mixture was stirred at -78° C. for 15 minutes
  2. temperaturewarmed to room temperature in 1 hour
  3. extractionextracted with ether
  4. extractionThe oil precipitate was extracted with ether
  5. extractionThe ether extract
  6. dry with materialwas dried (MgSO4)
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-2afac56649434d6e94367a7c34616f62
Quelldatensatz
uspto-grants-1990_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04921530

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