Sodium Cyanide → HCID 13882115, compound

HRID 543033Notes

Reaction equation

HRID 543033 reaction equation
[Cl:1][C:2]1[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[CH:16][C:3]=1[O:4][C:5]1[CH:15]=[CH:14][C:8]([O:9][CH:10]([CH3:13])[CH:11]=[O:12])=[CH:7][CH:6]=1.[C-:24]#[N:25].[Na+].[C:27](Cl)(=[O:31])[O:28][CH2:29][CH3:30].[C-]#N.[K+].C1OCCOCCOCCOCCOCCOC1>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)C.C(Cl)Cl>[CH2:29]([O:28][C:27]([O:12][CH:11]([CH:10]([O:9][C:8]1[CH:7]=[CH:6][C:5]([O:4][C:3]2[CH:16]=[CH:17][C:18]([C:20]([F:22])([F:21])[F:23])=[CH:19][C:2]=2[Cl:1])=[CH:15][CH:14]=1)[CH3:13])[C:24]#[N:25])=[O:31])[CH3:30]

Participants

9

Reactant 5

HCID 8929Sodium Cyanide2×HCID 9032Potassium CyanideHCID 10928Ethyl chloroformate3×HCID 2855718-Crown-6HCID 13882114HCID 13882114, compound

Product 1

HCID 13882115HCID 13882115, compound

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a 100 milliliter flask provided with a magnetic stirring bar and a drying tube were charged 0.5 gram of 2-[4-(2-chloro-4-trifluoromethylphenoxy)phenoxy]propionaldehyde, 0.5 gram of sodium cyanide, 0.12 gram of tetrabutyl ammonium hydrogen sulfate, 30 milliliters of methylene chloride and 0.2 milliliter of ethyl chlorocarbonate. After stirring overnight at room temperature, TLC analysis indicated the presence of a considerable amount of unreacted starting material so an additional 0.5 gram of sodium cyanide and 0.2 milliliter of ethyl chlorocarbonate were added and stirring was continued for 2.5 hours after which time an additional 0.2 milliliter of ethyl chlorocarbonate was added. After stirring an additional hour TLC indicated presence of some starting material so 1.0 gram of potassium cyanide and 0.1 gram of 18-crown-6 were added. After stirring at room temperature, an additional 1.5 hours, the reaction mixture was transferred to a separatory funnel, diluted with 150 milliliters of diethyl ether and washed with 4×50 milliliter portions of water. The organic layer was dried and evaporated affording about 1.0 gram of a brown, viscous residue. The residue was dissolved in methylene chloride and eluted over silica gel using methylene chloride as the eluent. The first four 50 milliliter fractions were combined and evaporated affording about 0.6 gram of colorless, gummy material confirmed by PMR analysis as the desired product.

Workup

  1. customTo a 100 milliliter flask provided with a magnetic stirring bar and a drying tube
  2. additionwere added
  3. stirringstirring
  4. waitwas continued for 2.5 hours
  5. stirringAfter stirring an additional hour TLC
  6. additionwere added
  7. stirringAfter stirring at room temperature, an additional 1.5 hours
  8. customthe reaction mixture was transferred to a separatory funnel
  9. washwashed with 4×50 milliliter portions of water
  10. customThe organic layer was dried
  11. customevaporated
  12. customaffording about 1.0 gram of a brown, viscous residue
  13. washeluted over silica gel
  14. customevaporated
  15. customaffording about 0.6 gram of colorless, gummy material

Sources & evidence

ORD record
ord-72ac87b8c85c4c1e8fc9d4d16c3fd935
Source dataset
uspto-grants-1987_04
Patent number
US04661149

Reaction notes

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