Piperidine → HCID 86679286, compound

HRID 1519727Notes

Reaction equation

HRID 1519727 reaction equation
[Cl:1][CH:2]=[CH:3]Cl.N1CCCCC1.[C:11]([C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][CH:14]=1)#[CH:12]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I.C1COCC1>[Cl:1]/[CH:2]=[CH:3]/[C:12]#[C:11][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][CH:14]=1

Participants

7

Reactant 3

HCID 8082PiperidineHCID 109001,2-DichloroethyleneHCID 27716454-Ethynylbenzaldehyde

Product 1

HCID 86679286HCID 86679286, compoundYield 59%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

1,2-Dichloroethylene (3.0 mL), tetrakis(triphenylphosphine)palladium (0.44 g), CuI (73 mg) and piperidine (1.1 mL) were added to a THF (20 mL) solution of 4-ethynylbenzaldehyde (1.0 g), and the mixture was stirred for 22.5 hours at room temperature in a nitrogen atmosphere. IPE was added, the insolubles were filtered out, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by OH type silica gel column chromatography (hexane/ethyl acetate/chloroform=9/1/1) to obtain 4-((E)-4-chlorobut-3-en-1-yn-1-yl)benzaldehyde (light brown solid) (0.87 g, 59%).

Workup

  1. additionIPE was added
  2. filtrationthe insolubles were filtered out
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe resulting residue was purified by OH type silica gel column chromatography (hexane/ethyl acetate/chloroform=9/1/1)

Sources & evidence

ORD record
ord-446f2abefa0b4ace916b6f70f41dda05
Source dataset
uspto-grants-2015_07
Patent number
US09073821B2

Reaction notes

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