Hydrochloric Acid → HCID 67202260, compound

HRID 547278Notes

Reaction equation

HRID 547278 reaction equation
[CH:1]([Mg]Cl)([CH3:3])[CH3:2].ClC([C:9]1[CH:14]=[CH:13]C=[CH:11][C:10]=1[CH:15]([CH3:18])[C:16]#[N:17])=O.Cl.CC[O:22][CH2:23][CH3:24]>C1COCC1.[Cl-].[Cl-].[Zn+2].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:23]([C:24]1[CH:11]=[C:10]([CH:15]([CH3:18])[C:16]#[N:17])[CH:9]=[CH:14][CH:13]=1)(=[O:22])[CH:1]([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 86625604HCID 86625604, compoundHCID 178418918HCID 178418918, compound

Product 1

HCID 67202260HCID 67202260, compoundYield 81%

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of ZnCl2 (0.390 g, 2.85 mmol) in 5 ml of dry THF at T=0° C. under nitrogen atmosphere commercial isopropylmagnesium chloride (2M in Et2O, 2.85 mL, 5.70 mmol) was added. After stirring 20 min the catalyst (dppf)PdCl2 (1%, 0.057 mmol) was added and, then, a solution of 2-(chlorocarbonyl)phenylpropionitrile (5.72 mmol), prepared as above described, in dry THF (5 mL) was added dropwise. The mixture was stirred 1 h at 0° C. then 3 h at room temperature. After cooling to 0° C., 3N HCl (10 mL) and Et2O (30 ml) were added. The aqueous layer was separated and the organic layer washed sequentially with a saturated solution of NaHCO3 (2×30 mL) and brine (30 mL). After drying on Na2SO4 and solvent evaporation under reduced pressure a residue was obtained that, after flash chromatography (eluent mixture n-hexane/EtOAc 95:5), afforded 2-[3-(isobutyryl)phenyl]propionitrile as pale yellow oil (0.804 g, 4.64 mmol). Yield 81%.

Workup

  1. additionwas added
  2. additionwas added
  3. additionwas added dropwise
  4. custom3 h
  5. customat room temperature
  6. temperatureAfter cooling to 0° C.
  7. customThe aqueous layer was separated
  8. washthe organic layer washed sequentially with a saturated solution of NaHCO3 (2×30 mL) and brine (30 mL)
  9. customAfter drying on Na2SO4 and solvent evaporation under reduced pressure a residue
  10. customwas obtained that, after flash chromatography (eluent mixture n-hexane/EtOAc 95:5)

Sources & evidence

ORD record
ord-b5ba2a756dca4b1fa093ba4ea91a7289
Source dataset
uspto-grants-2011_05
Patent number
US07939521B2

Reaction notes

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