Ethyl formate → 3,3-Bis(2-fluoro-4-methylphenyl)-2-(1-methyl-1H-tetrazol-5-yl)-2-propenal

HRID 1195376

Reaktionsgleichung

Reaktionsgleichung von HRID 1195376
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]([C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][C:18]=1[F:24])=[CH:10][C:11]1[N:15]([CH3:16])[N:14]=[N:13][N:12]=1.C([Li])CCC.[CH:30](OCC)=[O:31]>O1CCCC1>[F:24][C:18]1[CH:19]=[C:20]([CH3:23])[CH:21]=[CH:22][C:17]=1[C:9]([C:3]1[CH:4]=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=1[F:1])=[C:10]([C:11]1[N:15]([CH3:16])[N:14]=[N:13][N:12]=1)[CH:30]=[O:31]

Komponenten

5

Edukt 3

HCID 8025Ethyl formateHCID 147239931,1-Bis(2-fluoro-4-methylphenyl)-2-(1-methyl-1H-tetrazol-5-yl)etheneHCID 178418339Butyllithium

Produkt 1

HCID 147239943,3-Bis(2-fluoro-4-methylphenyl)-2-(1-methyl-1H-tetrazol-5-yl)-2-propenalAusbeute 37,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 1,1-bis(2-fluoro-4-methylphenyl)-2-(1-methyl-1H-tetrazol-5-yl)ethene (1.6 g, 5.0 mmoles) in tetrahydrofuran (20 mL) at -78° C. was added butyl lithium (2.3 mL of a 2.2M solution, 5 mmoles). After stirring for 15 minutes, ethyl formate (0.44 g, 6.0 mmoles) was added and the solution stirred with cooling for 2 hours. The reaction was quenched with 1N hydrochloric acid and the mixture extracted with diethyl ether. The extracts were dried (MgSO4) and evaporated. The residue was crystallized from isopropyl acetate to give 0.66 g of the title compound; m.p.=154°-155° C.

Aufarbeitung

  1. stirringthe solution stirred
  2. temperaturewith cooling for 2 hours
  3. customThe reaction was quenched with 1N hydrochloric acid
  4. extractionthe mixture extracted with diethyl ether
  5. dry with materialThe extracts were dried (MgSO4)
  6. customevaporated
  7. customThe residue was crystallized from isopropyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-9a7e5dc7dcd54c2aaf380ba819236d2a
Quelldatensatz
uspto-grants-1992_05
Patentnummer
US05110940

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