Quinoline → Ethyl alpha-Phenyl-alpha-styrylglycolate

HRID 358244

Reaction equation

HRID 358244 reaction equation
[C:1]1([C:7]([C:14]#[C:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([OH:13])[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C2C(=CC=CC=2)C=CC=1.[H][H]>[Pd].C(O)C>[C:1]1([C:7]([CH:14]=[CH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([OH:13])[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 7047QuinolineHCID 12328607Ethyl alpha-Phenyl-alpha-phenylethynylglycolateHCID 178418361HCID 178418361, compound2×

Product 1

HCID 53886882Ethyl alpha-Phenyl-alpha-styrylglycolate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Ethyl α-phenyl-α-phenylethynylglycolate (5.6 g., 0.02 mole) in 50 ml. of absolute ethanol, 0.2 g. of palladium on barium sulfate and a drop of quinoline were placed in a Parr shaker under 40 psi of hydrogen at room temperature. The required amount of hydrogen was taken up in 13 minutes. The catalyst was filtered and the filtrate stripped of ethanol in vacuo to yield 5.7 g. (100%) of crude product. Both n.m.r. and infrared spectroscopy confirmed the structure. The material was distilled to yield 4.1 g. of liquid, b.p. 130°-43° (0.16 mm.). N.m.r. analysis of the distilled material indicated that about 5 mole % of the fully saturated derivative was present as an impurity.

Workup

  1. filtrationThe catalyst was filtered
  2. customto yield 5.7 g
  3. distillationThe material was distilled
  4. customto yield 4.1 g

Sources & evidence

ORD record
ord-056e80740e334bb390aacf5d33ebd097
Source dataset
uspto-grants-1984_08
Patent number
US04465834

Linked notes

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