Dimethyl acetylenedicarboxylate → HCID 10022190, compound

HRID 2396036Notes

Reaction equation

HRID 2396036 reaction equation
[CH3:1][O:2][C:3]([C:5]#[C:6][C:7]([O:9][CH3:10])=[O:8])=[O:4].[CH3:11][Si:12]([CH3:24])([CH3:23])[O:13][C:14]([C:16]([O:18][Si:19]([CH3:22])([CH3:21])[CH3:20])=[CH2:17])=[CH2:15]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[CH2:17][C:16]([O:18][Si:19]([CH3:22])([CH3:21])[CH3:20])=[C:14]([O:13][Si:12]([CH3:23])([CH3:11])[CH3:24])[CH2:15][C:6]=1[C:7]([O:9][CH3:10])=[O:8])=[O:4]

Participants

4

Reactant 2

HCID 12980Dimethyl acetylenedicarboxylateHCID 45498662,3-Bis(trimethylsiloxy)-1,3-butadiene

Product 1

HCID 10022190HCID 10022190, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Under argon, a solution of 7.1 g (50 mmol) of acetylenedicarboxylic acid dimethyl ester in 30 ml of toluene is added dropwise to 12.5 g (50 mmol) of 2,3-bis(trimethylsilyloxy)-1,3-butadiene (95%) and then boiled under reflux for 19 hours. The reaction mixture is cooled, the solvent is evaporated off and the residue is distilled under a high vacuum (0.1 mbar,124°-127°), yielding the title compound in the form of a yellow, highly viscous oil, 1H-NMR (CDCl3): δ=0.18 (s, 18H), 3.09 (s, 4H), 3.78 (s, 6H).

Workup

  1. temperatureunder reflux for 19 hours
  2. temperatureThe reaction mixture is cooled
  3. customthe solvent is evaporated off
  4. distillationthe residue is distilled under a high vacuum (0.1 mbar,124°-127°)

Sources & evidence

ORD record
ord-26be43bb73d642cbb171def079a25efd
Source dataset
uspto-grants-1996_02
Patent number
US05491144

Reaction notes

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