Water → HCID 23103610, compound

HRID 2116496Notes

Reaction equation

HRID 2116496 reaction equation
[Br:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.C(N(C(C)C)C(C)C)C.[CH2:18]([Si:20]([CH2:28][CH3:29])([CH2:26][CH3:27])[CH2:21][CH2:22][O:23][CH2:24]Cl)[CH3:19].O>C(Cl)(Cl)Cl>[Br:1][C:2]1[C:7]([O:8][CH2:24][O:23][CH2:22][CH2:21][Si:20]([CH2:26][CH3:27])([CH2:18][CH3:19])[CH2:28][CH3:29])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 230702-Bromo-3-pyridinolHCID 81531DiisopropylethylamineHCID 23103608HCID 23103608, compound

Product 1

HCID 23103610HCID 23103610, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 2-bromo-3-hydroxypyridine (15 g, 0.0862 mol) in chloroform (260 mL), ethyldiisopropylamine (18 mL, 0.103 mol) and 2-(triethylsilyl)ethoxymethyl chloride (16.7 mL, 0.0948 mol) were added at 0° C. After the mixture was stirred at room temperature for 2 hours, water (50 mL) was added thereto and the precipitated insoluble materials were filtered off. The organic layer of the filtrate was separated, washed with water, and then dried over anhydrous magnesium sulfate. After the solvent was distilled off under reduced pressure, the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1) to give 2-bromo-3-[2-(triethylsilyl)ethoxymethoxy]pyridine (20.3 g, 77%) as a light-yellow oil.

Workup

  1. filtrationthe precipitated insoluble materials were filtered off
  2. customThe organic layer of the filtrate was separated
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationAfter the solvent was distilled off under reduced pressure
  6. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-ba64d3015e7b45f59d72d73d1c291d19
Source dataset
uspto-grants-2008_10
Patent number
US07439232B2

Reaction notes

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