Hydrochloric Acid → HCID 85977055, compound

HRID 2053764Notes

Reaction equation

HRID 2053764 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

HCID 85977055HCID 85977055, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-9e667978302d4e51bd4f9949ab87f864
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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