Water → Methyl 6-(1-hydroxyethyl)nicotinate

HRID 341518

Reaction equation

HRID 341518 reaction equation
[CH3:1][Mg]Br.[CH:4]([C:6]1[N:11]=[CH:10][C:9]([C:12]([O:14][CH3:15])=[O:13])=[CH:8][CH:7]=1)=[O:5].O>C1COCC1>[OH:5][CH:4]([C:6]1[N:11]=[CH:10][C:9]([C:12]([O:14][CH3:15])=[O:13])=[CH:8][CH:7]=1)[CH3:1]

Participants

5

Reactant 3

HCID 962WaterHCID 586269Methyl 6-formylpyridine-3-carboxylate2×HCID 178418573HCID 178418573, compound

Product 1

HCID 66803327Methyl 6-(1-hydroxyethyl)nicotinateYield 74.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl magnesium bromide (1M in THF) (3.03 mL, 3.03 mmol) was added drop wise to a solution of methyl 6-formylpyridine-3-carboxylate (Intermediate 195, 0.50 g, 3.03 mmol) in THF (20 mL) at −78 C. The reaction mixture was stirred at −78 C for 1 h and water (20 mL) was added. The mixture was warmed to room temperature and extracted with EtOAc (3×20 mL). The organic extracts were combined, dried over sodium sulfate, filtered and concentrated under vacuum to provide the title compound as an off-white solid (0.407 g, 74%). Method B HPLC-MS: MH+ requires m/z=182 Found: m/z=182, Rt=1.11 min (98%).

Workup

  1. extractionextracted with EtOAc (3×20 mL)
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-5cc4268f25ed4bad8db5369a66a82ca6
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Linked notes

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