Water → (Z)-2-((Z)-Dec-4-en-1-yl)dodec-6-enenitrile

HRID 530156Notes

Reaction equation

HRID 530156 reaction equation
CS(O[CH:6]([CH2:17][CH2:18][CH2:19]/[CH:20]=[CH:21]\[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:7][CH2:8][CH2:9]/[CH:10]=[CH:11]\[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])(=O)=O.[C-:27]#[N:28].[Na+].O>CN(C=O)C>[CH2:7]([CH:6]([CH2:17][CH2:18][CH2:19]/[CH:20]=[CH:21]\[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:27]#[N:28])[CH2:8][CH2:9]/[CH:10]=[CH:11]\[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 89768381(6Z,15Z)-henicosa-6,15-dien-11-yl methanesulfonate

Product 1

HCID 89768187(Z)-2-((Z)-Dec-4-en-1-yl)dodec-6-enenitrileYield 106%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (6Z,15Z)-henicosa-6,15-dien-11-yl methanesulfonate 5 (7.6 g, 19.6 mmol) and sodium cyanide (4.8 g, 98.1 mmol) in anhydrous DMF (60 mL) was heated to 60° C. overnight. Upon completion, the reaction mixture was poured into water (200 mL) and extracted with ethyl acetate (3×100 mL). The combine ethyl acetate extracts were washed with brine (3×100 mL), dried on magnesium sulfate, filtered and concentrated in vacuo to dryness. The product was purified by column chromatography (100% Hexanes to 1% ethyl acetate in hexanes) to afford (Z)-2-((Z)-dec-4-enyl)dodec-6-enenitrile 6 as a colorless oil (6.6 g, 97%). Rf 0.75 (10% EtOAc-Hexanes).

Workup

  1. extractionextracted with ethyl acetate (3×100 mL)
  2. washThe combine ethyl acetate extracts were washed with brine (3×100 mL)
  3. customdried on magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo to dryness
  6. customThe product was purified by column chromatography (100% Hexanes to 1% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-e24620fffbea487c85b5707146d5e6b2
Source dataset
uspto-grants-2016_05
Patent number
US09352042B2

Reaction notes

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