Cyclopropanecarbonitrile → 1-[2,6-Bis(methoxymethoxy)-3-methyl-phenyl]cyclopropanecarbonitrile

HRID 1484517Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1484517
F[C:2]1[C:7]([O:8][CH2:9][O:10][CH3:11])=[C:6]([CH3:12])[CH:5]=[CH:4][C:3]=1[O:13][CH2:14][O:15][CH3:16].[CH:17]1([C:20]#[N:21])[CH2:19][CH2:18]1.C[Si](N([K])[Si](C)(C)C)(C)C>C1(C)C=CC=CC=1>[CH3:11][O:10][CH2:9][O:8][C:7]1[C:6]([CH3:12])=[CH:5][CH:4]=[C:3]([O:13][CH2:14][O:15][CH3:16])[C:2]=1[C:17]1([C:20]#[N:21])[CH2:19][CH2:18]1

Komponenten

5

Edukt 3

HCID 79637CyclopropanecarbonitrileHCID 727043342-Fluoro-1,3-bis(methoxymethoxy)-4-methyl-benzene2×HCID 178504302HCID 178504302, Verbindung

Produkt 1

HCID 900148221-[2,6-Bis(methoxymethoxy)-3-methyl-phenyl]cyclopropanecarbonitrileAusbeute 42,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
105 °C

Versuchsvorschrift

2-fluoro-1,3-bis(methoxymethoxy)-4-methyl-benzene (Intermediate 34, 17.5 g, 76.011 mmol) and cyclopropanecarbonitrile (22.625 g, 337.23 mmol) were warmed under stirring to 105° C. A solution of [bis(trimethylsilyl)amino]potassium 0.5M in Toluene (275 ml) was slowly added for 1 hour to the previous solution. The reaction mixture was stirred for 6 hour at the same temperature. After cooling the solid was filtered off and the filtrate was partitioned between Brine (200 ml) and ethyl acetate (300 ml). The aqueous layer was re-extracted with ethyl acetate (200 ml) and combined organic layers were dried (Na2SO4), filtered and evaporated (the temperature during the concentration was ˜60° C. for removing the excess of cyclopropane carbonitrile). The residue was triturated with isopropanol (25 ml) and the solid collected and dried to afford the title compound (9.0 g) as white solid.

Aufarbeitung

  1. stirringThe reaction mixture was stirred for 6 hour at the same temperature
  2. temperatureAfter cooling the solid
  3. filtrationwas filtered off
  4. customthe filtrate was partitioned between Brine (200 ml) and ethyl acetate (300 ml)
  5. extractionThe aqueous layer was re-extracted with ethyl acetate (200 ml)
  6. dry with materialwere dried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated (the temperature during the concentration was ˜60° C.
  9. customfor removing the excess of cyclopropane carbonitrile)
  10. customThe residue was triturated with isopropanol (25 ml)
  11. customthe solid collected
  12. customdried

Quellen und Nachweise

ORD-Eintrag
ord-d48bf122405f4ceaaae32918cf85162e
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09422252B2

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