Water → HCID 15635484, compound

HRID 554551Notes

Reaction equation

HRID 554551 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1.[CH3:10][Si:11]([CH3:18])([CH3:17])[CH2:12][CH2:13][O:14][CH2:15]Cl.O>CCCCCC.C(COC)OC>[CH3:10][Si:11]([CH3:18])([CH3:17])[CH2:12][CH2:13][O:14][CH2:15][O:3][C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 962WaterHCID 79713-HydroxypyridineHCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl ether

Product 1

HCID 15635484HCID 15635484, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

Sodium hydride (3.85 g, 96.3 mmol) was washed with hexane and dimethoxyethane (90 mL) was added thereto. 3-Hydroxypyridine (4.97 g, 52.3 mmol) was added to the obtained mixture under cooling with ice over 10 minutes and the reaction mixture was stirred for 10 minutes, and then 2-(trimethylsilyl)ethoxymethyl chloride (10.0 mL, 56.5 mmol) was added thereto under cooling with ice over 25 minutes. The reaction mixture was stirred at room temperature for 14.5 hours. Under cooling with ice, to the reaction mixture was added water and the mixture was extracted with ether and the organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel flash column chromatography [developing solution=n-hexane:ethyl acetate (3:1)] to obtain the title product (10.8 g, 92%).

Workup

  1. additionwas added
  2. temperatureunder cooling with ice over 10 minutes
  3. temperatureunder cooling with ice over 25 minutes
  4. stirringThe reaction mixture was stirred at room temperature for 14.5 hours
  5. temperatureUnder cooling with ice, to the reaction mixture
  6. extractionthe mixture was extracted with ether
  7. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe obtained residue was purified by silica gel flash column chromatography [developing solution=n-hexane:ethyl acetate (3:1)]

Sources & evidence

ORD record
ord-c3ce733cf56f48e69896e16b69f58906
Source dataset
uspto-grants-2011_11
Patent number
US08048897B2

Reaction notes

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