1,3-Propanediol → HCID 86614999, compound

HRID 732390Notes

Reaction equation

HRID 732390 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([CH:10]=[O:11])[N:7]=[C:6]([Cl:12])[CH:5]=1.[CH2:14](O)[CH2:15][CH2:16][OH:17]>C1COCC1>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([CH:10]2[O:17][CH2:16][CH2:15][CH2:14][O:11]2)[N:7]=[C:6]([Cl:12])[CH:5]=1

Participants

4

Reactant 2

HCID 104421,3-PropanediolHCID 722138911006598-63-5

Product 1

HCID 86614999HCID 86614999, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve 2-chloro-6-formyl-isonicotinic acid methyl ester (200 mg, 1.0 mmol) in THF (8 mL). Add Amberlyst® 15 ion exchange resin (0.3 g) and dropwise 1,3-propanediol (0.1 mL, 1.5 mmol). Stir at room temperature for two days. Filter, concentrate and purify (silica gel chromatography, eluting with 0:100 to 10:90 ethyl acetate:hexanes) to give the title compound (88%).

Workup

  1. filtrationFilter
  2. concentrationconcentrate
  3. custompurify
  4. wash(silica gel chromatography, eluting with 0:100 to 10:90 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-80610f57d1bd44788ecf2f53c2f1ea99
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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