Methyl iodide → HCID 18799939, compound

HRID 1637768Notes

Reaction equation

HRID 1637768 reaction equation
[Cl:1][C:2]1[C:7]([OH:8])=[C:6]([CH:9]=[CH2:10])[CH:5]=[C:4]([CH:11]([OH:13])[CH3:12])[N:3]=1.[H-].[Na+].[CH3:16]I>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[C:7]([O:8][CH3:16])=[C:6]([CH:9]=[CH2:10])[CH:5]=[C:4]([CH:11]([OH:13])[CH3:12])[N:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 187998592-Chloro-3-hydroxy-4-vinyl-6-(1-hydroxyethyl)-pyridine

Product 1

HCID 18799939HCID 18799939, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-chloro-3-hydroxy-4-vinyl-6-(1-hydroxyethyl)-pyridine (1.46 g, 7.31 mmol) in 12 mL of N,N-dimethylformamide is treated with sodium hydride (292 mg, 60% in oil, 7.31 mmol) and stirred at room temperature for 1 h. The mixture is treated with methyl iodide (0.5 mL, 8.04 mmol) and stirred for 2 h. The reaction is diluted with 125 mL of ethyl acetate and washed with 4×50 mL of saturated sodium chloride. The organics are dried over potassium carbonate and concentrated in vacuo. The crude material is chromatographed over 150 g of silica gel (230-400 mesh), eluting with 25% ethyl acetate/hexanes to give 1.09 g (78%) of 2-chloro-3-methoxy-4-vinyl-6-(1-hydroxyethyl)-pyridine.

Workup

  1. stirringstirred for 2 h
  2. washwashed with 4×50 mL of saturated sodium chloride
  3. dry with materialThe organics are dried over potassium carbonate
  4. concentrationconcentrated in vacuo
  5. customThe crude material is chromatographed over 150 g of silica gel (230-400 mesh)
  6. washeluting with 25% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-2069a197a0484f98a32c8b47762208b7
Source dataset
uspto-grants-2000_03
Patent number
US06043248

Reaction notes

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