Phenylacetylene → HCID 86741680, compound

HRID 2119134Notes

Reaction equation

HRID 2119134 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[N:16]3[C@@H:11]([CH2:12][CH2:13][CH2:14][CH2:15]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[C:17]1([C:23]#[CH:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(N(CC)CC)C.C1COCC1>[C:17]1([C:23]#[C:24][C:2]2[CH:7]=[CH:6][C:5]([C@H:8]3[N:16]4[C@@H:11]([CH2:12][CH2:13][CH2:14][CH2:15]4)[CH2:10][CH2:9]3)=[CH:4][CH:3]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 10821PhenylacetyleneHCID 13606121HCID 13606121, compound

Product 1

HCID 86741680HCID 86741680, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

A 27.7 g (0.099 mole sample of trans-3-(4-bromophenyl)octahydroindolizine was dissolved in a mixture of 55 mL of triethylamine and 225 mL of dry THF under an atmosphere of argon and 12.1 g (0.12 mole) of phenylacetylene was added. Then 2.3 g (2 mmol) of tetrakistriphenylphosphine palladium (O) and 0.75 g 3.9 mmol) of cuprous iodide were added to the reaction mixture and the reaction refluxed overnight. An additional 1.2 g (1 mmol) of tetrakistriphenylphosphine palladium (O) and 0.38 g (1.9 mmol) of cuprous iodide were added to the reaction mixture and the mixture allowed to reflux overnight. The reaction was allowed to cool to room temperature, the mixture was filtered, and the THF evaporated in vacuo to a brown oil. The oil was partially dissolved in EtOAc and the insoluble material was filtered off. The EtOAc was evaporated in vacuo to an oil. The oil was flash chromatographed using 99% hexane, 1% EtOAc as the eluant. The major product bearing fractions were pooled, and the solvent evaporated in vacuo to give 12.5 g (42% yield) of the title compound as an oil.

Workup

  1. temperaturethe reaction refluxed overnight
  2. temperatureto reflux overnight
  3. filtrationthe mixture was filtered
  4. customthe THF evaporated in vacuo to a brown oil
  5. dissolutionThe oil was partially dissolved in EtOAc
  6. filtrationthe insoluble material was filtered off
  7. customThe EtOAc was evaporated in vacuo to an oil
  8. customchromatographed
  9. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-59050fea5a1b41b19985505292e70f45
Source dataset
uspto-grants-1987_07
Patent number
US04683239

Reaction notes

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