Dimethyl Sulfoxide → 7-Cyanoheptanoic acid ethyl ester

HRID 1039167Notes

Reaction equation

HRID 1039167 reaction equation
[C-:1]#[N:2].[Na+].[CH3:4][O:5][C:6](=[O:14])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]Br.[CH3:15]S(C)=O>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH2:4]([O:5][C:6](=[O:14])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:1]#[N:2])[CH3:15]

Participants

6

Reactant 3

HCID 679Dimethyl SulfoxideHCID 8929Sodium CyanideHCID 554086Methyl 7-bromoheptanoate

Product 1

HCID 862083227-Cyanoheptanoic acid ethyl esterYield 94%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Add sodium cyanide (12.5 g, 255 mmol) and tetra-n-butylammonium iodide (10 g, 27.0 mmol) portionwise to a solution of 7-bromoheptanoic acid methyl ester (25 g, 105 mmol) in DMSO (300 mL) at room temperature under nitrogen and heat the mixture at 50° C. for 4 hours. Cool the mixture and dilute with water (200 mL) and extract with diethyl ether (2×200 mL). Dry the combined organic extracts over sodium sulfate and remove the solvent under reduced pressure to provide 7-cyanoheptanoic acid ethyl ester (18.2 g, 94%).

Workup

  1. temperatureCool the mixture
  2. extractionextract with diethyl ether (2×200 mL)
  3. dry with materialDry the combined organic extracts over sodium sulfate
  4. customremove the solvent under reduced pressure

Sources & evidence

ORD record
ord-52483b8d9dae4875b64d5a825cb7ac2b
Source dataset
uspto-grants-2013_10
Patent number
US08552039B2

Reaction notes

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