Pyridine → Ethyl 5-chloromethyl-2,6-diisopropyl-4-(4-fluorophenyl)pyridine-3-carboxylate

HRID 1681256Notes

Reaction equation

HRID 1681256 reaction equation
N1C=CC=CC=1.S(Cl)([Cl:9])=O.[CH:11]([C:14]1[C:19]([C:20](OCC)=O)=[C:18]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[C:17]([CH2:32][OH:33])=[C:16]([CH:34]([CH3:36])[CH3:35])[N:15]=1)([CH3:13])[CH3:12].[C:37]([O:40]CC)(=O)[CH3:38]>O1CCCC1>[Cl:9][CH2:20][C:19]1[C:18]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)=[C:17]([C:32]([O:40][CH2:37][CH3:38])=[O:33])[C:16]([CH:34]([CH3:36])[CH3:35])=[N:15][C:14]=1[CH:11]([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 24386Thionyl ChlorideHCID 10291957Ethyl 2,6-Diisopropyl-4-(4-fluorophenyl)-3-hydroxymethylpyridine-5-carboxylate

Product 1

HCID 20081869Ethyl 5-chloromethyl-2,6-diisopropyl-4-(4-fluorophenyl)pyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.69 ml (20.9 mmol) of pyridine and 1.5 ml (20.9 mmol) of thionyl chloride are added successively at -5°0 C. to 5 g (13.9 mmol) of the compound from Example 4 dissolved in 100 m of dry tetrahydrofuran and the mixture is stirred for 15 minutes at the same temperature. The mixture is diluted using ethyl acetate and extracted several times using saturated sodium hydrogen carbonate solution, and the organic phases are dried over magnesium sulphate and concentrated in vacuo. The residue is chromatographed on a column (silica gel 70-230 mesh, in petroleum ether/ethyl acetate 95:5).

Workup

  1. additionThe mixture is diluted
  2. extractionextracted several times
  3. dry with materialthe organic phases are dried over magnesium sulphate
  4. concentrationconcentrated in vacuo
  5. customThe residue is chromatographed on a column (silica gel 70-230 mesh, in petroleum ether/ethyl acetate 95:5)

Sources & evidence

ORD record
ord-093ee5c1d8e74968bed94ba04d327451
Source dataset
uspto-grants-1992_12
Patent number
US05169857

Reaction notes

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