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

HRID 2053764ノート

反応式

HRID 2053764 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9e667978302d4e51bd4f9949ab87f864
出典データセット
uspto-grants-2008_02
特許番号
US07326791B2

反応ノート

読み込み中…