3-(1-Methoxyethenyl)hept-5-yn-2-one → HCID 86733881, compound

HRID 1834811Notes

Reaction equation

HRID 1834811 reaction equation
[CH3:1][O:2][C:3]([CH:5]([C:10](=[O:12])[CH3:11])[CH2:6][C:7]#[C:8][CH3:9])=[CH2:4].[H][H]>[Pd].CC([O-])=O.CC([O-])=O.[Pb+2].N1C2C(=CC=CC=2)C=CC=1.C(OCC)(=O)C>[CH3:1][O:2][C:3]([CH:5]([C:10](=[O:12])[CH3:11])[CH2:6]/[CH:7]=[CH:8]\[CH3:9])=[CH2:4]

Participants

6

Reactant 2

HCID 203721373-(1-Methoxyethenyl)hept-5-yn-2-oneHCID 178418361HCID 178418361, compound2×

Product 1

HCID 86733881HCID 86733881, compound

Reagents, catalysts & solvents 3

HCID 7047QuinolineCatalystHCID 131709914Lindlars catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 9.96 g. (60 mmol.) of 2-methoxy-3-acetyl-1-hepten-5-yne, 0.50 g. of Lindlar catalyst, and 10 drops of synthetic quinoline in 100 ml. of ethyl acetate was stirred under one atmosphere of hydrogen until hydrogen absorption was complete, then filtered, concentrated and distilled to afford (Z)-2-methoxy-3-acetyl-1,5-heptadiene; b.p. 64°-66°, (2.0 mmHg).

Workup

  1. additionA mixture of 9.96 g
  2. filtrationfiltered
  3. concentrationconcentrated
  4. distillationdistilled

Sources & evidence

ORD record
ord-08fcb61fc14e4a118c83d8a6859f5bbf
Source dataset
uspto-grants-1978_01
Patent number
US04071542

Reaction notes

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