Water → 3-Ethyl-3-(hydroxymethyl)pentanenitrile

HRID 1806970ノート

反応式

HRID 1806970 の反応式
[CH2:1]([C:3]1([CH2:10][CH3:11])[CH2:8]OS(=O)O[CH2:4]1)[CH3:2].[C-:12]#[N:13].[Na+].[OH2:15]>CS(C)=O>[CH2:1]([C:3]([CH2:8][OH:15])([CH2:10][CH3:11])[CH2:4][C:12]#[N:13])[CH3:2]

参加物

5

反応物 3

HCID 962WaterHCID 8929Sodium CyanideHCID 1990741,3-Propanediol, 2,2-diethyl-, cyclic sulfite (ester)

生成物 1

HCID 866404003-Ethyl-3-(hydroxymethyl)pentanenitrile収率 31%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
120 °C

実験手順

Step B To the solution of 5,5-diethyl-[1,3,2]dioxathiane 2-oxide (7 g, 39 mmol) in anhydrous dimethyl sulfoxide (40 mL) was added NaCN (3.9 g, 80 mmol). The reaction mixture was heated at 120° C. for 20 h. The mixture was cooled, and water was added. The mixture was extracted with ethyl acetate twice. The combined organic layers were washed with saturated aqueous NaHCO3 solution, brine, dried over MgSO4, and concentrated. The residue was purified by chromatography (EtOAc:hexanes=1:2) to give 3-ethyl-3-hydroxymethyl-pentanenitrile as a yellow oil (1.7 g, 31%).

後処理

  1. temperatureThe mixture was cooled
  2. extractionThe mixture was extracted with ethyl acetate twice
  3. washThe combined organic layers were washed with saturated aqueous NaHCO3 solution, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography (EtOAc:hexanes=1:2)

出典と根拠

ORDレコード
ord-417191957ec54f57b035c5f3595477f7
出典データセット
uspto-grants-2013_01
特許番号
US08354444B2

反応ノート

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