Potassium Carbonate → HCID 57424229, compound

HRID 1869885Notes

Reaction equation

HRID 1869885 reaction equation
[CH3:1][C:2]([CH3:28])([CH3:27])[CH2:3][O:4][C:5]([C:7]1[CH:8]=[C:9]([C:21]#[C:22][Si](C)(C)C)[CH:10]=[C:11]2[C:16]=1[O:15][C:14]([CH3:18])([CH3:17])[CH2:13][C:12]2([CH3:20])[CH3:19])=[O:6].C(=O)([O-])[O-].[K+].[K+]>CO>[CH3:1][C:2]([CH3:28])([CH3:27])[CH2:3][O:4][C:5]([C:7]1[CH:8]=[C:9]([C:21]#[CH:22])[CH:10]=[C:11]2[C:16]=1[O:15][C:14]([CH3:17])([CH3:18])[CH2:13][C:12]2([CH3:20])[CH3:19])=[O:6]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 69073779HCID 69073779, compound2×

Product 1

HCID 57424229HCID 57424229, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2,2,4,4-tetramethyl-6-trimethylsilanylethynylchroman-8-carboxylic acid 2,2-dimethylpropyl ester (Intermediate 47, 0.396 g, 1 mmol) in methanol (5 mL) was treated with potassium carbonate (1.4 g, 10 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 (0.227 g, 70%).

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-a566e6f80d784a5bb3ca11711ee82a55
Source dataset
uspto-grants-2009_12
Patent number
US07638648B2

Reaction notes

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