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

HRID 1090433노트

반응식

HRID 1090433 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 3776Isopropanol용매HCID 8028Tetrahydrofuran용매

실험 절차

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.).

후처리

  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

출처 및 근거

ORD 기록
ord-9d8e3d2b57464c57b0e284b9e7528080
출처 데이터셋
uspto-grants-1992_01
특허 번호
US05081271

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