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

HRID 31163ノート

反応式

HRID 31163 の反応式
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]

参加物

4

反応物 2

HCID 116165942-[(3-Methoxyphenyl)(1-naphthyl)methyl]malononitrileHCID 178424303HCID 178424303、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2307c2fb5b6e4357b26326685b3e00d7
出典データセット
uspto-grants-2008_09
特許番号
US07425580B2

反応ノート

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