3-Pyridinepropanol → 3-[3-[2-Hydroxy-3-(octadecyloxy)propoxy]propyl]-pyridine

HRID 1090338Notes

Reaction equation

HRID 1090338 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][CH2:9][OH:10])[CH:2]=1.[H-].[Na+].[O:13]1[CH:15]([CH2:16][O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH2:14]1>>[OH:13][CH:15]([CH2:16][O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH2:14][O:10][CH2:9][CH2:8][CH2:7][C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 178613-PyridinepropanolHCID 24758Sodium hydrideHCID 61831Oxirane, 2-[(octadecyloxy)methyl]-

Product 1

HCID 156827523-[3-[2-Hydroxy-3-(octadecyloxy)propoxy]propyl]-pyridineYield 40.8%

Procedure

To 3-pyridinepropanol (41.9 g), 60% oily sodium hydride (0.74 g) was added, followed by stirring at room temperature for 15 minutes. Crude 1,2-epoxy-3-octadecyloxypropane (10 g), an intermediate in Reference Example 1, was then added, followed by stirring at room temperature for 67 hours. The excess portion of the 3-pyridinepropanol was distilled off under reduced pressure. After adding a small volume of water to the residue, extraction was conducted with a mixture of hexane and ethyl acetate (1:1, 300 ml). After the extract was washed with water and dried, the solvent was distilled off. The resulting residue was purified by silica gel column chromatography (carrier, 250 g; developing solvent, hexane:ethyl acetate:acetone=4:1:0→3:1:1) to yield the desired compound (5.79 g).

Workup

  1. stirringby stirring at room temperature for 67 hours
  2. distillationThe excess portion of the 3-pyridinepropanol was distilled off under reduced pressure
  3. additionAfter adding a small volume of water
  4. extractionto the residue, extraction
  5. additionwas conducted with a mixture of hexane and ethyl acetate (1:1, 300 ml)
  6. washAfter the extract was washed with water
  7. customdried
  8. distillationthe solvent was distilled off
  9. customThe resulting residue was purified by silica gel column chromatography (carrier, 250 g; developing solvent, hexane:ethyl acetate:acetone=4:1:0→3:1:1)

Sources & evidence

ORD record
ord-279bc3a53ad0425e9f67d288fed0cb3d
Source dataset
uspto-grants-1992_01
Patent number
US05081245

Reaction notes

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