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

HRID 1806970노트

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HRID 1806970 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 866404003-Ethyl-3-(hydroxymethyl)pentanenitrile수율 31%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

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온도
120 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-417191957ec54f57b035c5f3595477f7
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08354444B2

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