Chloroacetone → HCID 86760890, compound

HRID 1987837Notes

Reaction equation

HRID 1987837 reaction equation
Cl[CH2:2][C:3](=O)[CH3:4].[Br-].[Li+].[CH3:8][O:9][CH2:10][C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][N:12]=1.C(N(CC)CC)C>CC(C)=O.C1(C)C=CC=CC=1.ClCCl.CO>[CH3:8][O:9][C:10]1[C:3]([CH3:4])=[CH:2][N:12]2[C:11]=1[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13]2

Participants

8

Reactant 4

HCID 6571Chloroacetone2×HCID 8471TriethylamineHCID 82050Lithium Bromide2×HCID 54209632HCID 54209632, compound

Product 1

HCID 86760890HCID 86760890, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 1140TolueneSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

1.46 mL (0.0174 mol) of chloroacetone are added to 1.5 g (0.0174 mol) of lithium bromide in 10 mL of acetone and the medium is stirred at room temperature for 15 minutes and then 1.5 g (0.00828 mol) of methyl 6-(methoxymethyl)nicotinate are added and the medium is heated under reflux overnight. 1.5 g (0.0174 mol) of lithium bromide and 1.46 mL (0.0174 mol) of chloroacetone are added to the reaction medium and the medium is kept under reflux for 5 hours. The medium is evaporated to dryness and the residue obtained is taken up in a dichloromethane-methanol (9-1) mixture. The insoluble material obtained is filtered and then 4.62 mL (0.033 mol) of triethylamine are added to the filtrate and the medium is stirred at room temperature for one hour. The reaction medium is concentrated. The residue obtained is taken up in toluene and the product is purified by filtration on a silica bed, eluting with toluene. After evaporation, 450 mg of a yellow solid are obtained.

Workup

  1. temperaturethe medium is heated
  2. temperatureunder reflux overnight
  3. temperatureunder reflux for 5 hours
  4. customThe medium is evaporated to dryness
  5. customthe residue obtained
  6. customThe insoluble material obtained
  7. filtrationis filtered
  8. stirringthe medium is stirred at room temperature for one hour
  9. concentrationThe reaction medium is concentrated
  10. customThe residue obtained
  11. filtrationthe product is purified by filtration on a silica bed
  12. washeluting with toluene
  13. customAfter evaporation, 450 mg of a yellow solid
  14. customare obtained

Sources & evidence

ORD record
ord-17d230eb6d8246799e191363c680e04c
Source dataset
uspto-grants-2009_06
Patent number
US07553845B2

Reaction notes

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