Pyridine → HCID 19063395, compound

HRID 2226296Notes

Reaction equation

HRID 2226296 reaction equation
[CH2:1]([OH:5])[CH2:2][CH2:3]O.[C:6](Cl)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.N1C=CC=CC=1.CC[O:34]CC>>[C:6]([O:34][O:5][CH2:1][CH2:2][CH3:3])([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 4

HCID 1049PyridineHCID 3283Diethyl Ether2×HCID 6456Trityl chlorideHCID 104421,3-Propanediol

Product 1

HCID 19063395HCID 19063395, compoundYield 46.4%

Procedure

1,3-Propanediol (1,053 g, 13.84 mmol), trityl chloride (3.50 g, 12.6 mmol) and anhydrous pyridine (5 ml) were combined in a flame-dried round-bottomed flask. The reaction mixture was stirred overnight at room temperature. Ether was added to the reaction mixture and the solution was extracted with H2O, 1N HCl, H2O, and brine. The ether layer was dried (MgSO4) and the solvent removed under reduced pressure. The crude product was purified by column chromatography (100 g silica gel; hexanes:ethyl acetate, gradient 8:1 to 6:1) to provide the pure ether compound 20, 1-O-trityloxy-propanol (1.85 g, 46.4% yield).

Workup

  1. extractionthe solution was extracted with H2O, 1N HCl, H2O, and brine
  2. dry with materialThe ether layer was dried (MgSO4)
  3. customthe solvent removed under reduced pressure
  4. customThe crude product was purified by column chromatography (100 g silica gel; hexanes:ethyl acetate, gradient 8:1 to 6:1)

Sources & evidence

ORD record
ord-d3c40c91af5d454bba9a537d120ff64e
Source dataset
uspto-grants-1994_09
Patent number
US05347030

Reaction notes

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