tert-Butyl bromoacetate → Tert-butyl {[6-(hydroxymethyl)pyridin-2-yl]oxy}acetate

HRID 1747066Notes

Reaction equation

HRID 1747066 reaction equation
[OH:1][CH2:2][C:3]1[NH:8][C:7](=[O:9])[CH:6]=[CH:5][CH:4]=1.Br[CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13]>[Ag]=O.CN(C=O)C>[OH:1][CH2:2][C:3]1[N:8]=[C:7]([O:9][CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 79177tert-Butyl bromoacetateHCID 224765516-(Hydroxymethyl)pyridin-2-ol

Product 1

HCID 59478892Tert-butyl {[6-(hydroxymethyl)pyridin-2-yl]oxy}acetateYield 72.8%

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.38 g of 6-(hydroxymethyl)pyridin-2(1H)-one, 2.15 g of tert-butyl bromoacetate, 3.07 g of silver oxide, and 33 mL of DMF was stirred at room temperature for 12 hours, and then at 60° C. for 12 hours. The insoluble material was separated by filtration and the filtrate was concentrated under reduced pressure. The residue was diluted with ethyl acetate, followed by washing with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate) to obtain 1.92 g of tert-butyl {[6-(hydroxymethyl)pyridin-2-yl]oxy}acetate as a yellow oily substance.

Workup

  1. waitat 60° C. for 12 hours
  2. customThe insoluble material was separated by filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionThe residue was diluted with ethyl acetate
  5. washby washing with a saturated aqueous sodium chloride solution
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate)

Sources & evidence

ORD record
ord-78d04c2d74ba4f4c88d41da85be53bbc
Source dataset
uspto-grants-2015_10
Patent number
US09150541B2

Reaction notes

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