Dimethyl Sulfoxide → Methyl 5-cyanopentanoate

HRID 2275982Notes

Reaction equation

HRID 2275982 reaction equation
[C-:1]#[N:2].[Na+].CS(C)=O.Br[CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14]>O>[C:1]([CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])#[N:2]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 8929Sodium CyanideHCID 79557Methyl 5-bromovalerate

Product 1

HCID 554130Methyl 5-cyanopentanoateYield 99.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

7.5 g (154 mmol) of sodium cyanide was added to 80 mL of dimethyl sulfoxide, and dissolved therein under heat at 90° C. 25.0 g (128 mmol) of methyl 5-bromovalerate was dropwise added to the solution at an inner temperature of 130° C. or lower, and stirred at 100° C. for 2 hours. After cooled to room temperature, 50 mL of water was added to this, which was then extracted with 60 mL of ethyl acetate. The organic layer was dried with magnesium sulfate, and the solvent was evaporated away under reduced pressure to give 18.0 g (yield 99%) of methyl 5-cyanovalerate.

Workup

  1. dissolutiondissolved
  2. temperatureAfter cooled to room temperature
  3. extractionwas then extracted with 60 mL of ethyl acetate
  4. dry with materialThe organic layer was dried with magnesium sulfate
  5. customthe solvent was evaporated away under reduced pressure

Sources & evidence

ORD record
ord-581d222cb21e44349561b95ce7ab7489
Source dataset
uspto-grants-2015_09
Patent number
US09130244B2

Reaction notes

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