Methyl 6-formylpyridine-3-carboxylate → Methyl 6-(1-hydroxyethyl)nicotinate

HRID 1427467Notes

Reaction equation

HRID 1427467 reaction equation
[CH:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][N:4]=1)=[O:2].[CH3:13][Mg]Br>O1CCCC1>[OH:2][CH:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][N:4]=1)[CH3:13]

Participants

4

Reactant 2

HCID 586269Methyl 6-formylpyridine-3-carboxylateHCID 178418573HCID 178418573, compound

Product 1

HCID 66803327Methyl 6-(1-hydroxyethyl)nicotinateYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a −78° C. solution of methyl 6-formylnicotinate (0.300 g, 1.82 mmol) in tetrahydrofuran (6 mL) was added methylmagnesium bromide (0.787 mL, 3M in THF, 2.36 mmol) over 20 minutes. The solution was warmed to 0° C. and stirred for 2 hours. The mixture was quenched with saturated ammonium chloride, extracted with ethyl acetate, dried over sodium sulfate, filtered and concentrated. Purification by preparative TLC gave methyl 6-(1-hydroxyethyl)nicotinate (230 mg, 70%) as a red oil. 1H NMR (400 MHz, CD3OD, δ): 8.93 (m, 1H), 8.26-8.29 (m, 1H), 7.59 (d, 1H), 4.73-4.83 (m, 1H), 3.84 (s, 3H), 1.37 (d, 3H).

Workup

  1. customThe mixture was quenched with saturated ammonium chloride
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by preparative TLC

Sources & evidence

ORD record
ord-67432db170d04811bdf1aa602ccbb2d2
Source dataset
uspto-grants-2015_01
Patent number
US08933104B2

Reaction notes

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