3,4-dihydro-2H-pyran → 2,3-Dichloro-5-{[(oxan-2-yl)oxy]methyl}pyridine

HRID 391357Notes

Reaction equation

HRID 391357 reaction equation
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2]1.O.O.[Sn](Cl)Cl.[Cl:12][C:13]1[C:18]([Cl:19])=[CH:17][C:16]([CH2:20][OH:21])=[CH:15][N:14]=1>C(Cl)(Cl)Cl>[Cl:12][C:13]1[C:18]([Cl:19])=[CH:17][C:16]([CH2:20][O:21][CH:6]2[CH2:5][CH2:4][CH2:3][CH2:2][O:1]2)=[CH:15][N:14]=1

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 61436Stannous chloride dihydrateHCID 21882961(5,6-Dichloropyridin-3-yl)methanol

Product 1

HCID 204835442,3-Dichloro-5-{[(oxan-2-yl)oxy]methyl}pyridine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3,4-Dihydro-2H-pyran (1.1 mL) and tin (II) chloride dihydrate (0.38 g) were added to a chloroform solution of 2,3-dichloro-5-hydroxymethylpyridine (1.5 g), and the reaction mixture was stirred at room temperature for 63 hours. The reaction mixture was filtered, and the solvent was then distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluate; n-hexane:ethyl acetate=100:0 to 90:10). The title compound (1.7 g) was obtained as colorless oil.

Workup

  1. filtrationThe reaction mixture was filtered
  2. distillationthe solvent was then distilled off under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (eluate; n-hexane:ethyl acetate=100:0 to 90:10)

Sources & evidence

ORD record
ord-e92f5479b5914b0cae0688e0c20a86fb
Source dataset
uspto-grants-2013_02
Patent number
US08383839B2

Reaction notes

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