Hydrochloric Acid → 3-Ethynyl-4-(pyrrolidin-1-ylcarbonyl)benzoic acid

HRID 2053764노트

반응식

HRID 2053764 반응식
[N:1]1([C:6]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14]C)=[O:13])=[CH:10][C:9]=2[C:18]#[C:19][Si](C)(C)C)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[K+].Cl>CO.O>[C:18]([C:9]1[CH:10]=[C:11]([CH:16]=[CH:17][C:8]=1[C:6]([N:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)=[O:7])[C:12]([OH:14])=[O:13])#[CH:19]

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 69309966Methyl 4-(pyrrolidin-1-ylcarbonyl)-3-(2-trimethylsilylethynyl)benzoate

생성물 1

HCID 859770553-Ethynyl-4-(pyrrolidin-1-ylcarbonyl)benzoic acid

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

7.70 g (23.4 mmol) of methyl 4-(pyrrolidin-1-ylcarbonyl)-3-(2-trimethylsilylethynyl)benzoate is dissolved in 30 mL of methanol, combined with 46.7 mL (93.4 mmol) 2 molar potassium hydroxide solution, and refluxed for 2 hours. After the elimination of volatile constituents in vacuo, the residue is diluted with demineralized water and acidified with 2 molar hydrochloric acid solution. The aqueous phase is extracted three times with ethyl acetate, the combined organic phases are dried over sodium sulfate, and then the solvent is eliminated in vacuo. Yield: 3.14 g (55%); Rf value: 0.59 (silica gel; dichloromethane/ethanol=4:1); C14H13NO3 (243.27); mass spectrum: (M+H)+=244.

후처리

  1. temperaturerefluxed for 2 hours
  2. extractionThe aqueous phase is extracted three times with ethyl acetate
  3. dry with materialthe combined organic phases are dried over sodium sulfate

출처 및 근거

ORD 기록
ord-9e667978302d4e51bd4f9949ab87f864
출처 데이터셋
uspto-grants-2008_02
특허 번호
US07326791B2

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