2-[(3-Methoxyphenyl)(1-naphthyl)methyl]malononitrile → 2-[(2-Methylphenyl)(1-naphthyl)methyl]malononitrile

HRID 31163Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 31163
CO[C:3]1[CH:4]=[C:5]([CH:9]([C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17][CH:16]=2)[CH:10]([C:13]#[N:14])[C:11]#[N:12])[CH:6]=[CH:7][CH:8]=1.[C:25]1(C)C=CC=CC=1[Mg]Br>O1CCCC1>[CH3:25][C:6]1[CH:7]=[CH:8][CH:3]=[CH:4][C:5]=1[CH:9]([C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1)[CH:10]([C:13]#[N:14])[C:11]#[N:12]

Komponenten

4

Edukt 2

HCID 116165942-[(3-Methoxyphenyl)(1-naphthyl)methyl]malononitrileHCID 178424303HCID 178424303, Verbindung

Produkt 1

HCID 115076382-[(2-Methylphenyl)(1-naphthyl)methyl]malononitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A flask was charged with (1-naphthalenylmethylene)-propanedinitrile of Example 3 (408 mg, 2 mmol) and 10 mL anhydrous tetrahydrofuran. To this stirred solution was added, at room temperature, ortho-tolyl magnesium bromide (1.2 mL, 2.4 mmol, 2 M in tetrahydrofuran). The reaction was stirred 1.5 hours, after which it was quenched with 1 N hydrochloric acid and taken up in ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate, brine, dried over magnesium sulfate, filtered, and evaporated to dryness. Following purification on silica (20% ethyl acetate/hexanes) 455 mg product was isolated as an off white foam.

Aufarbeitung

  1. additionTo this stirred solution was added, at room temperature
  2. customafter which it was quenched with 1 N hydrochloric acid
  3. washThe organic layer was washed with saturated aqueous sodium bicarbonate, brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. custompurification on silica (20% ethyl acetate/hexanes) 455 mg product
  8. customwas isolated as an off white foam

Quellen und Nachweise

ORD-Eintrag
ord-2307c2fb5b6e4357b26326685b3e00d7
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425580B2

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