反応 #5583

反応方程式

2-benzyl-1,4-naphthoquinone

Malononitrile

potassium hydride

hexane

→

product

収率 38.0%

2-Amino-4-benzyl-3-cyano-5-hydroxynaphtho[1,2-b]furan

収率 38.0%

溶媒

hexane ethyl acetate

tetrahydrofuran

tetrahydrofuran

反応条件

後処理

1. 1
   その他Solvent was decanted off
2. 2
   workup.ADDITIONwas then added to the slurry dropwise
3. 3
   workup.ADDITIONwas then added dropwise
4. 4
   温度to cool to room temperature
5. 5
   その他quenched with methanol (50 ml)
6. 6
   workup.ADDITIONThe mixture was poured into water (100 ml)
7. 7
   抽出extracted into ethyl acetate (3 x 250 ml)
8. 8
   乾燥The organic layer was dried (magnesium sulfate)
9. 9
   その他evaporated to an oil

実験手順

A mixture of potassium hydride (7.56 g, 63 mmol, 35% oil dispersion) and hexane (250ml) was stirred at room temperature under nitrogen. Solvent was decanted off and substituted with dry tetrahydrofuran (250ml). Malononitrile (4.16 g, 63 mmol), dissolved in tetrahydrofuran (50 ml), was then added to the slurry dropwise. A mixture of 2-benzyl-1,4-naphthoquinone (15.62 g, 63 mmol) and tetrahydrofuran (50 ml) was then added dropwise. The reaction mixture was set at reflux for 2h, allowed to cool to room temperature and quenched with methanol (50 ml). The mixture was poured into water (100 ml) and extracted into ethyl acetate (3 x 250 ml). The organic layer was dried (magnesium sulfate) and evaporated to an oil. Chromatography (silica gel: hexane/ethyl acetate (2 : 1) as eluant) of the oily residue afforded 7.48 g (23 mmol, 38%) of product as green crystals, m.p. 224°-225 ° C.; 1H NMR (d6DMSO): 4.5(s,2H), 7.1-7.6 (m, 7H), 7.9(d, 1H), 9.25(s, 1H); IR (nujol): 3460, 3310, 3240, 3190, 2220; High resolution mass spectrum: calculated 314.1055, measured 314.1061.

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