Dimethyl acetylenedicarboxylate → 4,5-Bis(trimethylsilyloxy)cyclohexa-1,4-diene-1,2-dicarboxylic acid dimethyl ester

HRID 1376750ノート

反応式

HRID 1376750 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

HCID 100221904,5-Bis(trimethylsilyloxy)cyclohexa-1,4-diene-1,2-dicarboxylic acid dimethyl ester

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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).

後処理

  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°)

出典と根拠

ORDレコード
ord-34ba917782ad4fe1a8b29a276481cf59
出典データセット
uspto-grants-1997_09
特許番号
US05663336

反応ノート

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