Citric Acid → HCID 45121755, compound

HRID 1799762Notes

Reaction equation

HRID 1799762 reaction equation
C(=O)([O-])[O-].[K+].[K+].C[Si](C)(C)[C:9]#[C:10][C:11]1[S:15][CH:14]=[N:13][C:12]=1[CH2:16][OH:17].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO>[C:10]([C:11]1[S:15][CH:14]=[N:13][C:12]=1[CH2:16][OH:17])#[CH:9]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 11430Potassium CarbonateHCID 592179795-[2-(Trimethylsilyl)ethynyl]-4-thiazolemethanol

Product 1

HCID 45121755HCID 45121755, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium carbonate (39 mg) was added to a solution of 6.02 g of [5-[2-(trimethylsilyl)ethynyl]thiazol-4-yl]-methanol in 12 ml of methanol, and the mixture was stirred at room temperature for 10 min. A 10% aqueous citric acid solution (6 ml) was added thereto, and the mixture was stirred for 30 min. The reaction mixture was then extracted with 90 ml of ethyl acetate. The organic layer was washed with 12 ml of 5% sodium bicarbonate water and 12 ml of 20% brine in that order and was treated with 0.8 g of activated carbon and anhydrous magnesium sulfate. Toluene (15 ml) was added to the organic layer, the mixture was concentrated, and the precipitated solid was collected by filtration to give 3.11 g of 5-ethynyl-4-hydroxymethylthiazole.

Workup

  1. stirringthe mixture was stirred for 30 min
  2. extractionThe reaction mixture was then extracted with 90 ml of ethyl acetate
  3. washThe organic layer was washed with 12 ml of 5% sodium bicarbonate water and 12 ml of 20% brine in that order
  4. additionwas treated with 0.8 g of activated carbon and anhydrous magnesium sulfate
  5. additionToluene (15 ml) was added to the organic layer
  6. concentrationthe mixture was concentrated
  7. filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-db57c2b0e9314ec09bd3df024103c871
Source dataset
uspto-grants-2013_01
Patent number
US08344154B2

Reaction notes

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