Water → 1,1-Dimethylethyl 2-(3-pyridinylmethoxy)acetate

HRID 1007175Notes

Reaction equation

HRID 1007175 reaction equation
[H-].[Na+].[N:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][OH:10])[CH:4]=1.Br[CH:12](C)[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].O>C1COCC1>[N:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][O:10][CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 75103-PyridinemethanolHCID 24758Sodium hydrideHCID 545327tert-Butyl 2-bromopropanoate

Product 1

HCID 247635281,1-Dimethylethyl 2-(3-pyridinylmethoxy)acetateYield 59.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a suspension of 1.24 g of sodium hydride (60% oil dispersion; 31 mmol) in 90 mL of THF were added dropwise 3.27 g of 3-pyridinemethanol (30 mmol) in 10 mL of dry THF at room temperature over 5 min. The resulting white suspension was stirred at room temperature for an hour, to which was then added dropwise 6.27 g of tert-butyl 2-bromopropionate (30 mmol) in 10 mL of dry THF at room temperature over 5 min. The mixture was stirred at room temperature for 11.5 hours. After adding water, the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried and evaporated. The residue was purified by column chromatography on silica gel (eluent: n-hexane:ethyl acetate=1:1) to give 4.01 g of tert-butyl (pyridin-3-yl)methoxyacetate (Yield: 56.3%) as a dark brown oil.

Workup

  1. stirringThe mixture was stirred at room temperature for 11.5 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. customdried
  5. customevaporated
  6. customThe residue was purified by column chromatography on silica gel (eluent: n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-06e8215504cd42109096efffce44afa7
Source dataset
uspto-grants-2004_09
Patent number
US06794392B1

Reaction notes

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