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

HRID 604952Notes

Reaction equation

HRID 604952 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-4f8e123e22d1463d8951fd04b028cd7e
Source dataset
uspto-grants-2011_03
Patent number
US07910751B2

Reaction notes

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