Potassium Carbonate → HCID 57424232, compound

HRID 1869890Notes

Reaction equation

HRID 1869890 reaction equation
[C:1]([O:5][C:6]([C:8]1[CH:9]=[C:10]([C:22]#[C:23][Si](C)(C)C)[CH:11]=[C:12]2[C:17]=1[O:16][C:15]([CH3:19])([CH3:18])[CH2:14][C:13]2([CH3:21])[CH3:20])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+]>CO>[C:1]([O:5][C:6]([C:8]1[CH:9]=[C:10]([C:22]#[CH:23])[CH:11]=[C:12]2[C:17]=1[O:16][C:15]([CH3:19])([CH3:18])[CH2:14][C:13]2([CH3:21])[CH3:20])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 69079068HCID 69079068, compound2×

Product 1

HCID 57424232HCID 57424232, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2,2,4,4-tetramethyl-6-trimethylsilanylethynylchroman-8-carboxylic acid tert-butyl ester (Intermediate 51, 0.064 g, 0.17 mmol) in methanol (5 mL) was treated with potassium carbonate (0.23 g, 1.7 mmol) and the resulting reaction mixture was stirred at ambient temperature for 30 minutes. The solvent was evaporated in vacuo, the residue was diluted with water and extracted with ethyl acetate. The organic phase was washed with brine, dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to afford the title compound as a brown oil (0.051 g, 97%).

Workup

  1. customthe resulting reaction mixture
  2. customThe solvent was evaporated in vacuo
  3. additionthe residue was diluted with water
  4. extractionextracted with ethyl acetate
  5. washThe organic phase was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-86e670cd9ee44e35a7860598c73c8b91
Source dataset
uspto-grants-2009_12
Patent number
US07638648B2

Reaction notes

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