Potassium Carbonate → HCID 57424258, compound

HRID 1765844Notes

Reaction equation

HRID 1765844 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[C:5]([CH3:19])([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]#[C:14][Si](C)(C)C)[CH:8]=1)[CH3:6])[CH3:2].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH2:1]([O:3][C:4](=[O:20])[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]#[CH:14])[CH:8]=1)([CH3:6])[CH3:19])[CH3:2]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 57424257HCID 57424257, compound2×

Product 1

HCID 57424258HCID 57424258, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-methyl-2-(3-trimethylsilanylethynyl-phenyl)-propionic acid ethyl ester (Intermediate 131, 0.74 g, 2.56 mmol) in ethanol (10 mL) was treated with potassium carbonate (0.2 g, 1.45 mmol). The resulting reaction mixture was stirred at ambient temperature overnight. The volatiles were evaporated in vacuo and the residue was diluted with water and extracted with diethyl ether. The organic phase was washed with water and brine, dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to a residue that was subjected to flash column chromatography over silica gel (230–400 mesh) using 1–5% ethyl acetate in hexane as the eluent to afford the title product (0.4 g, 72%).

Workup

  1. customThe resulting reaction mixture
  2. customThe volatiles were evaporated in vacuo
  3. additionthe residue was diluted with water
  4. extractionextracted with diethyl ether
  5. washThe organic phase was washed with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customevaporated in vacuo to a residue that

Sources & evidence

ORD record
ord-e9bd5776bd584bf78ec4530753b57e51
Source dataset
uspto-grants-2007_06
Patent number
US07226951B2

Reaction notes

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