Hexanal → Oct-2-enenitrile

HRID 1505475Notes

Reaction equation

HRID 1505475 reaction equation
CC(C)([O-])C.[K+].[C:7]([CH2:9]P(=O)(OCC)OCC)#[N:8].[CH:18](=O)[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]>O1CCCC1>[C:7](#[N:8])[CH:9]=[CH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

5

Reactant 3

HCID 6184HexanalHCID 75676Diethyl (cyanomethyl)phosphonateHCID 23665647Potassium tert-butoxide

Product 1

HCID 54249989Oct-2-enenitrileYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of 1.0 M of potassium tert-butoxide in tetrahydrofuran (165 mL, 0.165 mol) at 0° C. was added dropwise a solution of diethyl cyanomethylphosphonate (27 mL, 0.17 mol) in tetrahydrofuran (100 mL). The reaction was warmed to room temperature and then cooled to 0° C. again after stirring for 30 min. To the reaction mixture was added a solution of hexanal (18 mL, 0.15 mol) in tetrahydrofuran (150 mL). The reaction was stirred overnight, allowed to warm up to room temperature. The reaction was quenched with water and extracted with ethyl acetate (EtOAc). The combined organic layers were washed with brine, dried over MgSO4, concentrated, and purified on silica gel (eluting with 0 to 15% EtOAc in hexanes) to provide the desired product (˜17 g, 92%) as a mixture of cis and trans isomers. MS calculated for C8H14N(M+H)+: m/z=124.113. Found: 124.3.

Workup

  1. temperaturecooled to 0° C. again
  2. stirringThe reaction was stirred overnight
  3. temperatureto warm up to room temperature
  4. customThe reaction was quenched with water
  5. extractionextracted with ethyl acetate (EtOAc)
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated
  9. custompurified on silica gel (eluting with 0 to 15% EtOAc in hexanes)

Sources & evidence

ORD record
ord-97c03f637e2947eda8a8ed996b3ffded
Source dataset
uspto-grants-2015_12
Patent number
US09216984B2

Reaction notes

Loading…