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

HRID 31163Notes

Reaction equation

HRID 31163 reaction equation
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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-2307c2fb5b6e4357b26326685b3e00d7
Source dataset
uspto-grants-2008_09
Patent number
US07425580B2

Reaction notes

Loading…