Methyl iodide → Methyl 2-[3-methoxy-5-(trifluoromethyl)phenyl]propanoate

HRID 1686423Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1686423
[CH3:1][O:2][C:3](=[O:17])[CH2:4][C:5]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[C:7]([O:15][CH3:16])[CH:6]=1.[CH2:18]([Li])CCC.C(NC(C)C)(C)C.IC>C1COCC1.Cl>[CH3:16][O:15][C:7]1[CH:6]=[C:5]([CH:4]([CH3:18])[C:3]([O:2][CH3:1])=[O:17])[CH:10]=[C:9]([C:11]([F:13])([F:12])[F:14])[CH:8]=1

Komponenten

7

Edukt 4

HCID 6328Methyl iodideHCID 7912DiisopropylamineHCID 86625038Methyl[3-methoxy-5-(trifluoromethyl)phenyl]acetateHCID 178418339Butyllithium

Produkt 1

HCID 66734169Methyl 2-[3-methoxy-5-(trifluoromethyl)phenyl]propanoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The product from step (i) (1.3 g) was added to a pre-formed solution of butyllithium (2.5M in hexanes, 2.51 ml), diisopropylamine (0.88 ml) in dry THF (30 ml) at −78° C. The mixture was kept at −78° C. for 1 hour before adding iodomethane (0.4 ml). The mixture was slowly allowed to warm to room temperature overnight. The mixture was diluted with 2M HCl, extracted with ether, dried (MgSO4) and evaporated under reduced pressure to give an oil. The oil was purified by flash column chromatography (eluent 2:1 isohexane/diethylether) (0.8 g).

Aufarbeitung

  1. extractionextracted with ether
  2. dry with materialdried (MgSO4)
  3. customevaporated under reduced pressure
  4. customto give an oil
  5. customThe oil was purified by flash column chromatography (eluent 2:1 isohexane/diethylether) (0.8 g)

Quellen und Nachweise

ORD-Eintrag
ord-3ef2069adf84451ab34d3d7c868106b0
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08148572B2

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