Chloride → HCID 19611576, compound

HRID 1602490Notes

Reaction equation

HRID 1602490 reaction equation
[C:1]([C:5]1[N:6]=[C:7]([CH2:10][OH:11])[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].CC(C)([O-])C.[K+].[Cl-].Cl[C:20]1[N:25]=[C:24]([C:26]([O:28][CH3:29])=[O:27])[CH:23]=[CH:22][CH:21]=1>O>[C:1]([C:5]1[N:6]=[C:7]([CH2:10][O:11][C:20]2[N:25]=[C:24]([C:26]([O:28][CH3:29])=[O:27])[CH:23]=[CH:22][CH:21]=2)[S:8][CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 312ChlorideHCID 242723Methyl 6-chloropicolinateHCID 22063786HCID 22063786, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 19611576HCID 19611576, compoundYield 25.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 4-tert-butyl-2-(hydroxymethyl)thiazole (441 mg, 2.57 mmol), potassium-tert-butoxide (580 mg, 5.17 mmol), tricaprylmethylamminium chloride (100 mg) and methyl 6-chloropyridine-2-carboxylate (660 mg, 3.85 mmol) was stirred at 120° C. for 2 hours. Water was added to the reaction solution and the product formed was extracted with ethyl acetate. The extract was washed with water and brine in that order, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent =hexane:ethyl acetate=20:1 to 10:1) to give methyl 6-(4-tert-butyl-2-thiazolylmethoxy)pyridine-2-carboxylate (198 mg, 0.65 mmol, 25%).

Workup

  1. customthe product formed
  2. extractionwas extracted with ethyl acetate
  3. washThe extract was washed with water and brine in that order
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (eluent =hexane:ethyl acetate=20:1 to 10:1)

Sources & evidence

ORD record
ord-200de3802a1e4a1fa16fb0dad7fc6f06
Source dataset
uspto-grants-1999_11
Patent number
US05981559

Reaction notes

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