Methanol → 3-Bromo-6-methoxy-2-[(methoxymethoxy)methyl]pyridine

HRID 2353331Notes

Reaction equation

HRID 2353331 reaction equation
[Br:1][C:2]1[C:3]([CH2:10][OH:11])=[N:4][C:5]([O:8][CH3:9])=[CH:6][CH:7]=1.C(N(C(C)C)CC)(C)C.[CH3:21][O:22][CH2:23]Cl.CO>C(Cl)Cl>[Br:1][C:2]1[C:3]([CH2:10][O:11][CH2:21][O:22][CH3:23])=[N:4][C:5]([O:8][CH3:9])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 11769918(3-Bromo-6-methoxypyridin-2-yl)methanol

Product 1

HCID 672418193-Bromo-6-methoxy-2-[(methoxymethoxy)methyl]pyridineYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-bromo-2-hydroxymethyl-6-methoxypyridine (10.6 g, 48.6 mmol) synthesized by the method described in Organic & Biomolecular Chemistry 1 (16) 2865-2876 (2003) in methylene chloride (150 mL) was successively added dropwise with diisopropylethylamine (31.4 g, 243 mmol) and chloromethyl methyl ether (13.3 g, 165 mmol) under ice cooling. The mixture was warmed to room temperature, stirred for 16 hours, and then added with methanol (30 mL), and the mixture was stirred for 30 minutes. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=30:1→20:1) to obtain 3-bromo-6-methoxy-2-(methoxymethyloxy)methylpyridine (12.1 g, 95%) as pale yellow oil.

Workup

  1. stirringthe mixture was stirred for 30 minutes
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=30:1→20:1)

Sources & evidence

ORD record
ord-d835ebd44ab74d74bb2ae0e1b1e58cad
Source dataset
uspto-grants-2010_07
Patent number
US07750019B2

Reaction notes

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