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

HRID 1806970Notes

Reaction equation

HRID 1806970 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-417191957ec54f57b035c5f3595477f7
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

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