1,3-Propanediol → HCID 11171851, compound

HRID 2103744Notes

Reaction equation

HRID 2103744 reaction equation
[CH2:1]([OH:5])[CH2:2][CH2:3][OH:4].[Na].[Cl:7][C:8]1[CH:15]=[C:14](F)[CH:13]=[CH:12][C:9]=1[C:10]#[N:11]>O>[Cl:7][C:8]1[CH:15]=[C:14]([O:4][CH2:3][CH2:2][CH2:1][OH:5])[CH:13]=[CH:12][C:9]=1[C:10]#[N:11]

Participants

5

Reactant 3

HCID 104421,3-PropanediolHCID 1090002-Chloro-4-fluorobenzonitrileHCID 5360545Sodium

Product 1

HCID 11171851HCID 11171851, compoundYield 50.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 1,3-propanediol (320 mg, 4.2 mmol) was added sodium (21 mg, 0.92 mmol). The mixture is stirred at room temperature for 10 minutes and 2-chloro-4-fluoro-benzonitrile (156 mg, 1.0 mmol) was added. The reaction was heated to 105° C. for 24 hours. The reaction was cooled to room temperature, was diluted with water and was extracted with Et2O (3×). The organic solution was dried (MgSO4), filtered and concentrated. The residue was purified by reverse phase high pressure chromatography eluting with a solvent gradient (15% of 0.1% formic acid/CH3CN in 0.1% formic acid/water to 100% of 0.1% formic acid/water) to provide 107 mg of 2-chloro-4-(3-hydroxy-propoxy)-benzonitrile. 1H NMR (CDCl3) δ 7.54 (d, 1H), 7.00 (m, 1H), 6.85 (dd, 1H), 4.15 (t, 2H), 3.83 (t, 2H), 2.04 (m, 2H).

Workup

  1. temperatureThe reaction was heated to 105° C. for 24 hours
  2. temperatureThe reaction was cooled to room temperature
  3. extractionwas extracted with Et2O (3×)
  4. dry with materialThe organic solution was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by reverse phase high pressure chromatography
  8. washeluting with a solvent gradient (15% of 0.1% formic acid/CH3CN in 0.1% formic acid/water to 100% of 0.1% formic acid/water)

Sources & evidence

ORD record
ord-a4649740d7e84ed2ba08f7f533829273
Source dataset
uspto-grants-2009_08
Patent number
US07576128B2

Reaction notes

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