Phenylacetylene → HCID 10241049, compound

HRID 1902188Notes

Reaction equation

HRID 1902188 reaction equation
C(=O)(O[CH2:6][C:7](=[CH2:9])[CH3:8])OCC.[C:11]1([C:17]#[CH:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>O1CCCC1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[CH2:8]([C:18]#[C:17][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:7](=[CH2:6])[CH3:9]

Participants

5

Reactant 2

HCID 10821PhenylacetyleneHCID 11094742ethyl methallyl carbonate2×

Product 1

HCID 10241049HCID 10241049, compoundYield 61.5%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl methallyl carbonate (1.58 g, 0.011 mole), phenylacetylene (1.02 g, 0.010 mole) and tetrakis(triphenylphosphine) palladium (O) (0.25 g, 0.21 mmole) in tetrahydrofuran (15 ml) was refluxed for 91 hours under N2. Gas chromatographic analysis showed that the ethyl methallyl carbonate was totally consumed but about 10 percent of phenylacetylene remained. The product, methallylphenylacetylene, was isolated by preparative gas chromatography (0.96 g, 61.5 percent yield) and identified by spectroscopic techniques.

Workup

  1. temperaturewas refluxed for 91 hours under N2
  2. customwas totally consumed

Sources & evidence

ORD record
ord-b05d7cc4920c4989a675da8ddec4bcfc
Source dataset
uspto-grants-1982_12
Patent number
US04362670

Reaction notes

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