Acrylonitrile → HCID 68151383, compound

HRID 1400274Notes

Reaction equation

HRID 1400274 reaction equation
P(C1C=CC=CC=1)(C)C.FC(F)(F)S(O[C:16]1[CH:25]=[CH:24][C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]=1[Cl:26])(=O)=O.[C:29](#[N:32])[CH:30]=[CH2:31].C(N(CC)CC)C>CC([O-])=O.CC([O-])=O.[Pd+2].C(#N)C>[Cl:26][C:17]1[C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:24]=[CH:25][C:16]=1/[CH:31]=[CH:30]/[C:29]#[N:32]

Participants

7

Reactant 4

HCID 7855AcrylonitrileHCID 8471TriethylamineHCID 69597DimethylphenylphosphineHCID 12095458HCID 12095458, compound

Product 1

HCID 68151383HCID 68151383, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Procedure

Pd(OAc)2 (3 mol %, 11 mg), PMe2Ph (5 mol %, 11 mg), 1-chloronaphthalen-2-yl trifluoromethanesulfonate (500 mg, 1.61 mmol), acrylonitrile (103 mg, 1.93 mmoli), triethylamine (242 mg, 2.4 mmol) and 15 mL of acetonitrile were added to a microvawe vial and the mixture was irradiated by MW at 120° C. for 1 h. At the conclusion of the reaction, the solvent was evaporated under reduced pressure and the residue was treated with dichloromethane and washed with water; the organic layer was filtered through a pad of silica gel with copious washings, concentrated, and purified by flash chromatography on silica gel eluted with petroleum ether/ethyl acetate (93:7) to give (2E)-3-(1-chloronaphthalen-2-yl)prop-2-enenitrile as colourless oil (120 mg, 35% yield).

Workup

  1. customthe mixture was irradiated by MW at 120° C. for 1 h
  2. customAt the conclusion of the reaction
  3. customthe solvent was evaporated under reduced pressure
  4. additionthe residue was treated with dichloromethane
  5. washwashed with water
  6. filtrationthe organic layer was filtered through a pad of silica gel with copious washings
  7. concentrationconcentrated
  8. custompurified by flash chromatography on silica gel
  9. washeluted with petroleum ether/ethyl acetate (93:7)

Sources & evidence

ORD record
ord-58046a7bcf154baaa911d96bda66597c
Source dataset
uspto-grants-2014_12
Patent number
US08906946B2

Reaction notes

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