1-Acetoxy-2-bromoethane → HCID 12254004, compound

HRID 352205Notes

Reaction equation

HRID 352205 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1.Br[CH2:11][CH2:12][O:13][C:14](=[O:16])[CH3:15]>CN(C=O)C>[CH2:12]([O:13][C:14](=[O:16])[CH2:15][O:3][C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1)[CH3:11]

Participants

5

Reactant 3

HCID 135641-Acetoxy-2-bromoethaneHCID 24758Sodium hydrideHCID 178418642HCID 178418642, compound

Product 1

HCID 12254004HCID 12254004, compoundYield 9.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a slurry of sodium hydride, 1.73 g (43.2 mmol) in 100 mL of DMF was added 3.4 g (36.0 mmol) of 4-hydroxypyridine. The mixture was stirred 10 minutes then added to a solution of 3.3 mL (30.0 mmol) of bromoethylacetate in 100 mL DMF. The reaction mixture was stirred 72 hours at rt. then concentrated to dryness. The residue was partitioned between 20% isopropanol/chloroform and water and washed with saturated aqueous NaHCO3, washed with brine, dried over Na2SO4, filtered and concentrated to dryness. The residue was purified by radial chromatography using MeOH/chloroform as eluent and concentrated to dryness to yield 510 mg (9.4%) of the desired product as a tan oil. 1H—NMR is consistent with structure. MS (ion spray) 182.1 (M+).

Workup

  1. stirringThe reaction mixture was stirred 72 hours at rt
  2. concentrationthen concentrated to dryness
  3. customThe residue was partitioned between 20% isopropanol/chloroform and water
  4. washwashed with saturated aqueous NaHCO3
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated to dryness
  9. customThe residue was purified by radial chromatography
  10. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-83cda7b195dc4c1aa8ceafac668766a1
Source dataset
uspto-grants-2004_06
Patent number
US06743794B2

Reaction notes

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