Benzyl Alcohol → 2-Benzyloxy-3-(2,3-epoxypropoxy)-pyridine

HRID 444450Notes

Reaction equation

HRID 444450 reaction equation
[H-].[Na+].[O:3]1[CH2:16][CH:4]1[CH2:5][O:6][C:7]1[C:8]([N+]([O-])=O)=[N:9][CH:10]=[CH:11][CH:12]=1.[CH2:17]([OH:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>COCCOC>[CH2:17]([O:24][C:8]1[C:7]([O:6][CH2:5][CH:4]2[O:3][CH2:16]2)=[CH:12][CH:11]=[CH:10][N:9]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 11183186Pyridine, 2-nitro-3-(oxiranylmethoxy)-(9CI)

Product 1

HCID 234638152-Benzyloxy-3-(2,3-epoxypropoxy)-pyridine

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

3.6 g of a sodium hydride suspension (55%) are added in portions, at 0°-5°, to 15.7 g of 3-(2,3-epoxypropoxy)-2-nitro-pyridine and 9.0 g of benzyl alcohol dissolved in 150 ml of 1,2-dimethoxyethane, with stirring and cooling, and the mixture is stirred for a further 3 hours at 0°-5° and for 2 hours at 20°-25°. The reaction mixture is evaporated, the residue is dissolved in ethyl acetate, the solution is washed with water and the ethyl acetate solution is evaporated. The residue (20 g) is chromatographed on 400 g of silica gel and eluted with toluene (250 ml fractions). 2-Benzyloxy-3-(2,3-epoxypropoxy)-pyridine is obtained in the form of an oil from fractions 28-36.

Workup

  1. temperaturecooling
  2. stirringthe mixture is stirred for a further 3 hours at 0°-5° and for 2 hours at 20°-25°
  3. customThe reaction mixture is evaporated
  4. dissolutionthe residue is dissolved in ethyl acetate
  5. washthe solution is washed with water
  6. customthe ethyl acetate solution is evaporated
  7. customThe residue (20 g) is chromatographed on 400 g of silica gel
  8. washeluted with toluene (250 ml fractions)

Sources & evidence

ORD record
ord-660e70befc5c401887fdec753b98e39b
Source dataset
uspto-grants-1981_04
Patent number
US04264599

Reaction notes

Loading…