Methyl iodide → 4-(Methoxymethyl)benzonitrile

HRID 1771285

反応式

HRID 1771285 の反応式
[OH:1][CH2:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1.[H-].[Na+].CI.[C:15](OCC)(=O)C.CCCCCC>C1COCC1.O>[CH3:15][O:1][CH2:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1

参加物

7

反応物 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 160549p-Cyanobenzyl alcoholHCID 21226206Ethyl acetate hexane

生成物 1

HCID 132851414-(Methoxymethyl)benzonitrile収率 90%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

4-(Hydroxymethyl)benzonitrile (6.0 g, 45.09 mmol) was dissolved in THF (60 mL), cooled to −5° C. to −10° C. and treated with sodium hydride (2.16 g, 90.19 mmol). The resulting mixture was stirred for 30 minutes then treated with methyl iodide (9.6 g, 67.65 mmol) at RT for 2 hours. After completion of the reaction (TLC; ethyl acetate/Hexane, 5:5), the mixture was poured into water (50 mL) and extracted with ethyl acetate (3×25 mL). The separated organic layers were combined, dried over Na2SO4 and concentrated in vacuo. The crude compound was purified by gradient flash chromatography, eluting with 5% ethyl acetate in hexane to afford 4-(methoxymethyl)benzonitrile (6.7 g, 90%).

後処理

  1. temperaturecooled to −5° C. to −10° C.
  2. extractionextracted with ethyl acetate (3×25 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe crude compound was purified by gradient flash chromatography
  6. washeluting with 5% ethyl acetate in hexane

出典と根拠

ORDレコード
ord-295ea34f25804b15a70de710a3432545
出典データセット
uspto-grants-2016_02
特許番号
US09249130B2

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