3,4-Dimethoxybenzophenone → Methyl 3-(3,4-Dimethoxyphenyl)-3-phenylacrylate

HRID 583440

反応式

HRID 583440 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([C:17]2[CH:22]=[CH:21][C:20](OC)=[C:19](OC)[CH:18]=2)=[CH:12][C:13]([O:15][CH3:16])=[O:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].COC1C=C(C=CC=1OC)C(C1C=CC=CC=1)=O.CC(P(OC)(O)=O)(C([O-])=O)C.C[Si](C)(C)[N-][Si](C)(C)C.[Li+]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[CH:12][C:13]([O:15][CH3:16])=[O:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

参加物

5

反応物 4

HCID 2867423,4-DimethoxybenzophenoneHCID 2733832Lithium HexamethyldisilazideHCID 9820154Methyl 3,3-bis-(3,4-dimethoxyphenyl)acrylateHCID 53413272Trimethylphosphonoacetate

生成物 1

HCID 54371031Methyl 3-(3,4-Dimethoxyphenyl)-3-phenylacrylate

実験手順

Methyl 3-(3,4-Dimethoxyphenyl)-3-phenylacrylate was prepared analogously to methyl 3,3-bis-(3,4-dimethoxyphenyl)acrylate using 3,4-dimethoxybenzophenone (4.8 g, 20 mmol), trimethylphosphonoacetate (4.1 g, 22 mmol) and lithium hexamethyldisilazide (22 mL, 22 mmol, 1 M) with a reaction time of 138 hours at reflux. The crude mixture was purified by flash column chromatography (silica gel, 1% ethyl acetate/methylene chloride) to afford 14.39 g (73%) of a mixture of the E and Z isomers as an oil. The isomers were separated by additional purification (silica gel, 1% ethyl acetate/methylene chloride) to afford pure samples of each of the isomers.

後処理

  1. customwith a reaction time of 138 hours
  2. temperatureat reflux
  3. customThe crude mixture was purified by flash column chromatography (silica gel, 1% ethyl acetate/methylene chloride)

出典と根拠

ORDレコード
ord-83eb26e9272c43958eb32cb66b52f3ac
出典データセット
uspto-grants-1999_07
特許番号
US05929117

関連ノート

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