Acrylonitrile → HCID 12294966, compound

HRID 1085605Notes

Reaction equation

HRID 1085605 reaction equation
[C:1](#[N:4])[CH:2]=[CH2:3].C[Si]([CH2:9][N:10]=[C:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[SH-]C)(C)C>C1COCC1>[C:14]1([C:11]2[CH2:3][CH:2]([C:1]#[N:4])[CH2:9][N:10]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 7855AcrylonitrileHCID 178504146HCID 178504146, compound

Product 1

HCID 12294966HCID 12294966, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-5 °C

Procedure

A solution of acrylonitrile (0.65 mL; 0.01 mol) and N-(trimethylsilyl)methyl-S-methyl-benzenethioimidate (2.4 g; 0.01 mol) in THF (100 mL) is cooled to -5° C. in an ice-acetone bath. Under a nitrogen purge, a solution of tetrabutylammonium fluoride (1.0 mL of a 1 N solution in THF) and THF (20 mL) is added dropwise over 30 minutes. The solution is stirred another 30 minutes at -5° C., and then allowed to warm slowly to ambient. Stirring is continued another 18 hours, and then solvent is removed under reduced pressure. The residue is partitioned between ether/water and the water layer extracted with fresh ether. The combined organic layer is washed with water, then saturated sodium chloride. The solution is dried over MgSO4, and cooling the filtrate causes precipitation of an off-white solid (1.2 g; 70% theoretical yield) whose spectral characteristics are identical to the material described by Tsuge [J. Org. Chem. 52, 2523 (1987)].

Workup

  1. customUnder a nitrogen purge
  2. additiona solution of tetrabutylammonium fluoride (1.0 mL of a 1 N solution in THF) and THF (20 mL) is added dropwise over 30 minutes
  3. temperatureto warm slowly to ambient
  4. stirringStirring
  5. waitis continued another 18 hours
  6. customsolvent is removed under reduced pressure
  7. customThe residue is partitioned between ether/water
  8. extractionthe water layer extracted with fresh ether
  9. washThe combined organic layer is washed with water
  10. dry with materialThe solution is dried over MgSO4
  11. temperaturecooling
  12. customthe filtrate causes precipitation of an off-white solid (1.2 g; 70% theoretical yield) whose spectral characteristics

Sources & evidence

ORD record
ord-6c9406b6f7eb4178a0d3967e43ccf39f
Source dataset
uspto-grants-1991_04
Patent number
US05010098

Reaction notes

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