Potassium Carbonate → HCID 57424226, compound

HRID 1869880Notes

Reaction equation

HRID 1869880 reaction equation
[CH:1]([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])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+]>CO>[CH:1]([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]([CH3:18])([CH3:17])[CH2:13][C:12]2([CH3:20])[CH3:19])=[O:6])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 69073742HCID 69073742, compound2×

Product 1

HCID 57424226HCID 57424226, compoundYield 13.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2,2,4,4-tetramethyl-6-trimethylsilanylethynylchroman-8-carboxylic acid isopropyl ester (Intermediate 43, 0.23 g, 0.62 mmol) in methanol (5 mL) was treated with potassium carbonate (0.85 g, 6.2 mmol) and the resulting reaction mixture was stirred at ambient temperature overnight. The solvent was evaporated in vacuo, the residue was diluted with water and extracted with diethyl ether. The organic phase was washed with brine, dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to a brown oil that was subjected to flash column chromatography over silica gel (230-400 mesh) using 20% ethyl acetate in hexane as the eluent to afford the title compound (0.0246 g, 13%).

Workup

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

Sources & evidence

ORD record
ord-1090d9f9549b4f8cacbbf70c33f72efe
Source dataset
uspto-grants-2009_12
Patent number
US07638648B2

Reaction notes

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