Potassium Carbonate → HCID 22499791, compound

HRID 858870Notes

Reaction equation

HRID 858870 reaction equation
C[O:2][C:3](=[O:20])[CH:4]([Cl:19])[C:5](=[O:18])[CH2:6][C:7]([CH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)(O)[CH2:8][CH2:9][C:10]#[CH:11].C([O-])([O-])=O.[K+].[K+]>CO>[CH2:8]([C:7]1([CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17]2)[O:20][C:3](=[O:2])[CH:4]([Cl:19])[C:5](=[O:18])[CH2:6]1)[CH2:9][C:10]#[CH:11]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 587622142-Chloro-5-cyclopentyl-5-hydroxy-3-oxo-non-8-ynoic Acid Methyl Ester

Product 1

HCID 22499791HCID 22499791, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A slurry of 2-chloro-5-cyclopentyl-5-hydroxy-3-oxo-non-8-ynoic acid methyl ester (6.0 g, 20 mmol) from Step 3 above and K2CO3 (11 g, 80 mmol) in methanol (100 mL) was stirred at 50° C. for 1.5 hours. The reaction was concentrated by rotary evaporation, and then re-dissolved in ethyl acetate. The solution was washed with water, and then saturated Na2CO3. The organic layer was dried over sodium sulfate. After removing the solids by filtration, the organic layer was concentrated by rotary evaporation to yield the desired product (5.24 g, 97% yield).

Workup

  1. concentrationThe reaction was concentrated by rotary evaporation
  2. dissolutionre-dissolved in ethyl acetate
  3. washThe solution was washed with water
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customAfter removing the solids
  6. filtrationby filtration
  7. concentrationthe organic layer was concentrated by rotary evaporation

Sources & evidence

ORD record
ord-5abbafba22dc4e10b8dd40191bbdfc01
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

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