3-Pentanol → 2-[6-(1-Ethyl-propoxy)-2,5-dimethylpyrimidin-4-yl]-2-(2,4,6-trimethylphenyl)-propionitrile

HRID 1737674ノート

反応式

HRID 1737674 の反応式
[CH3:1][CH2:2][CH:3]([OH:6])[CH2:4][CH3:5].[H-].[Na+].Cl[C:10]1[N:15]=[C:14]([CH3:16])[N:13]=[C:12]([C:17]([C:21]2[C:26]([CH3:27])=[CH:25][C:24]([CH3:28])=[CH:23][C:22]=2[CH3:29])([CH3:20])[C:18]#[N:19])[C:11]=1[CH3:30]>C1COCC1>[CH2:2]([CH:3]([O:6][C:10]1[N:15]=[C:14]([CH3:16])[N:13]=[C:12]([C:17]([C:21]2[C:22]([CH3:29])=[CH:23][C:24]([CH3:28])=[CH:25][C:26]=2[CH3:27])([CH3:20])[C:18]#[N:19])[C:11]=1[CH3:30])[CH2:4][CH3:5])[CH3:1]

参加物

5

反応物 3

HCID 114283-PentanolHCID 24758Sodium hydrideHCID 219123342-(6-Chloro-2,5-dimethylpyrimidin-4-yl)-2-(2,4,6-trimethylphenyl)-propionitrile

生成物 1

HCID 219122012-[6-(1-Ethyl-propoxy)-2,5-dimethylpyrimidin-4-yl]-2-(2,4,6-trimethylphenyl)-propionitrile収率 145.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 3-pentanol (140 mg, 1.59 mmol) in 2 ml of dry THF was added sodium hydride (60% in oil, 38 mg) and the mixture was stirred at room temperature for 5 minutes. 2-(6--Choro-2,5-dimethylpyrimidin-4-yl)-2-(2,4,6-trimethylphenyl)-propionitrile (100 mg, 0.319 mmol) was added to the reaction mixture, and the resulting mixture was heated at reflux for 4 hours. The mixture was quenched with water and extracted with ethyl acetate. The organic layer was separated, dried and concentrated to give a brown oil (170 mg). The residue was purified through chromatotron using 20% ethyl cetate in hexane as eluent to give a mixture of two isomers as a yellow glass form and oth having a M+ of 365 from GC/Ms. 1H NMR (CDCl3) δ6.8 and 6.76 (s, 2H), 4.08 and 3.96 (m, 1H), 3.25 and 3.22 (s, 3H), 2.36 and 2.30 (s, 3H), 2.21, 2.20 and 2.06 (s, total of 9H), 1.5-1.7 (m, 4H), 1.04 (s, 3H), 0.96 and 0.90 (t, 3H) ppm.

後処理

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 4 hours
  3. customThe mixture was quenched with water
  4. extractionextracted with ethyl acetate
  5. customThe organic layer was separated
  6. customdried
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-dfdbad7faa7d4f2280fb51ee604db31b
出典データセット
uspto-grants-1999_10
特許番号
US05962479

反応ノート

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