Hydrochloric Acid → 4-[3-(3,5-Bistrimethylgermylphenyl)-3-oxo-1-propenyl]benzoic Acid

HRID 1090433ノート

反応式

HRID 1090433 の反応式
[CH3:1][Ge:2]([CH3:17])([CH3:16])[C:3]1[CH:4]=[C:5]([C:13](=[O:15])[CH3:14])[CH:6]=[C:7]([Ge:9]([CH3:12])([CH3:11])[CH3:10])[CH:8]=1.[CH:18]([C:20]1[CH:29]=[CH:28][C:23]([C:24]([O:26]C)=[O:25])=[CH:22][CH:21]=1)=O.[OH-].[K+].Cl>C(O)(C)C.O1CCCC1>[CH3:11][Ge:9]([CH3:10])([CH3:12])[C:7]1[CH:6]=[C:5]([C:13](=[O:15])[CH:14]=[CH:18][C:20]2[CH:29]=[CH:28][C:23]([C:24]([OH:26])=[O:25])=[CH:22][CH:21]=2)[CH:4]=[C:3]([Ge:2]([CH3:16])([CH3:1])[CH3:17])[CH:8]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 15294Methyl 4-FormylbenzoateHCID 128849113',5'-Bis(trimethylgermyl)acetophenone

生成物 1

HCID 1308244-[3-(3,5-Bistrimethylgermylphenyl)-3-oxo-1-propenyl]benzoic Acid収率 53.7%

試薬・触媒・溶媒 2

HCID 3776Isopropanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

3',5'-Bis(trimethylgermyl)acetophenone 163 mg (0.46 mmol) and 96 mg (0.58 mmol) of methyl 4-formylbenzoate was dissolved in 4 ml of a mixture of isopropanol and tetrahydrofuran (1:1). To the mixture was added 2.5 ml of 0.75N aqueous potassium hydroxide solution with stirring and the mixture was stirred at room temperature overnight. The reaction mixture was adjusted to pH3.8 with 0.2N hydrochloric acid and extracted with AcOEt. The extract was evaporated. The residue was purified by column chromatography on silicagel [eluent: methylene chloride-MeOH (10:1)] and recrystallized from a mixture of methylene chloride, MeOH and n-hexane to give 120 mg of yellow prisms, m.p.194°-195.5° C. (dec.).

後処理

  1. stirringthe mixture was stirred at room temperature overnight
  2. extractionextracted with AcOEt
  3. customThe extract was evaporated
  4. customThe residue was purified by column chromatography on silicagel [eluent: methylene chloride-MeOH (10:1)]
  5. customrecrystallized from a mixture of methylene chloride, MeOH and n-hexane

出典と根拠

ORDレコード
ord-9d8e3d2b57464c57b0e284b9e7528080
出典データセット
uspto-grants-1992_01
特許番号
US05081271

反応ノート

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