3-Hydroxypyridine → HCID 15635484, compound

HRID 2116481Notes

Reaction equation

HRID 2116481 reaction equation
[H-].[Na+].C(COC)OC.[OH:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1.[CH3:16][Si:17]([CH3:24])([CH3:23])[CH2:18][CH2:19][O:20][CH2:21]Cl>CCCCCC.O>[CH3:16][Si:17]([CH3:24])([CH3:23])[CH2:18][CH2:19][O:20][CH2:21][O:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1

Participants

7

Reactant 4

HCID 79713-HydroxypyridineHCID 80711,2-DimethoxyethaneHCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl ether

Product 1

HCID 15635484HCID 15635484, compoundYield 84.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8058HexaneSolvent

Procedure

Sodium hydride (5.55 g, 139 mmol) was washed with hexane and then mixed with dimethoxyethane (200 ml). To the resulting mixture, 3-hydroxypyridine (12.0 g, 126 mmol) was added over 10 minutes under ice cooling. After stirring for 10 minutes, 2-(trimethylsilyl)ethoxymethyl chloride (25.2 g, 151 mmol) was added over 25 minutes under ice cooling. After stirring at room temperature for 14.5 hours, the reaction mixture was diluted with water under ice cooling and extracted with ether. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=67:33) to give 3-[2-(trimethylsilyl)ethoxymethoxy]pyridine (23.9 g, 84%) as a brown oil.

Workup

  1. stirringAfter stirring at room temperature for 14.5 hours
  2. extractionextracted with ether
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=67:33)

Sources & evidence

ORD record
ord-46c3c2947ea1491cb1cc1054319323b5
Source dataset
uspto-grants-2008_10
Patent number
US07439232B2

Reaction notes

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