Methyl iodide → 4-(Methoxymethyl)benzonitrile

HRID 2059738

Reaktionsgleichung

Reaktionsgleichung von HRID 2059738
[OH:1][CH2:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1.I[CH3:12].[H-].[Na+]>CN(C=O)C>[CH3:12][O:1][CH2:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 160549p-Cyanobenzyl alcohol

Produkt 1

HCID 132851414-(Methoxymethyl)benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 4-(hydroxymethyl)benzonitrile (5 g, 37.6 mmol) in DMF (100 mL) was added iodomethane (7.03 mL, 113 mmol) and NaH (1.502 g, 37.6 mmol). The reaction aged at rt for 2 h and was then partitioned between EtOAc and H2O. The organic layer was separated and washed with H2O (2×), brine, dried (MgSO4), filtered and concentrated. The residue was purified by flash chromatography on silica gel gradient eluted with 0-20% EtOAc/hexane to afford the title compound. HPLC/MS: 148.1 (M+1); Rt=2.28 min.

Aufarbeitung

  1. customwas then partitioned between EtOAc and H2O
  2. customThe organic layer was separated
  3. washwashed with H2O (2×), brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography on silica gel gradient
  8. washeluted with 0-20% EtOAc/hexane

Quellen und Nachweise

ORD-Eintrag
ord-06dfa702d7c04da1a7a774eb4e012a2a
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08278304B2

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