Triethylamine → 4-Hydroxymethyl-2-(3,4,5-trimethoxyphenyl-ethynyl)pyridine

HRID 1634900Notes

Reaction equation

HRID 1634900 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]#[C:14][C:15]2[CH:20]=[C:19]([C:21](O)=[O:22])[CH:18]=[CH:17][N:16]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].C(N(CC)CC)C.ClC(OCC)=O.C(OCC)(=O)C>C1COCC1>[OH:22][CH2:21][C:19]1[CH:18]=[CH:17][N:16]=[C:15]([C:14]#[C:13][C:5]2[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)[CH:20]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 10928Ethyl chloroformateHCID 186750082-(3,4,5-Trimethoxyphenylethynyl)pyridine-4-carboxylic Acid

Product 1

HCID 186749764-Hydroxymethyl-2-(3,4,5-trimethoxyphenyl-ethynyl)pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(3,4,5-Trimethoxyphenylethynyl)pyridine-4-carboxylic acid (90 mg) was dissolved in THF (6 mL), and to the solution triethylamine (35 mg) was added at 0° C. under an argon atmosphere. Ethyl chloroformate (34 mg) was then added to the mixture, and the mixture was stirred for 1 hour. Ethyl acetate was added to the reaction mixture, and the mixture was washed with water and saturated brine and dried over anhydrous sodium sulfate. After concentrating the reaction mixture, the residue was dissolved in THF (2 mL), and to the solution an aqueous solution (1 mL) of sodium borohydride (16 mg) was added at 0° C., and the resultant mixture was stirred for 1 hour. The reaction mixture was extracted with ethyl acetate, and the resultant organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. After concentrating the organic layer under reduced pressure, the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1 to ethyl acetate) to obtain the title compound.

Workup

  1. washthe mixture was washed with water and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationAfter concentrating the reaction mixture
  4. dissolutionthe residue was dissolved in THF (2 mL)
  5. additionto the solution an aqueous solution (1 mL) of sodium borohydride (16 mg) was added at 0° C.
  6. stirringthe resultant mixture was stirred for 1 hour
  7. extractionThe reaction mixture was extracted with ethyl acetate
  8. washthe resultant organic layer was washed with saturated brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationAfter concentrating the organic layer under reduced pressure
  11. customthe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1 to ethyl acetate)

Sources & evidence

ORD record
ord-a4eadff269a34244bbd624bf318589af
Source dataset
uspto-grants-2003_01
Patent number
US06509329B1

Reaction notes

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