Methyl 6-formylpyridine-3-carboxylate → HCID 67981010, compound

HRID 1427445Notes

Reaction equation

HRID 1427445 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].[CH2:13]([Mg]Br)[CH:14]([CH3:16])[CH3:15]>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)[CH2:13][CH:14]([CH3:16])[CH3:15]

Participants

4

Reactant 2

HCID 586269Methyl 6-formylpyridine-3-carboxylateHCID 178418816HCID 178418816, compound2×

Product 1

HCID 67981010HCID 67981010, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

To a −10° C. solution of methyl 6-formylnicotinate (800 mg, 4.8 mmol) in tetrahydrofuran was added isobutylmagnesium bromide (3.6 mL, 7.2 mmol, 2.0M in THF). The resulting mixture was stirred at −10° C. After 2 hours, additional isobutylmagnesium bromide (2.4 mL, 4.8 mmol) was added and the reaction was stirred at −10° C. for another 2 hours. The reaction was quenched with water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered and concentrated to a brown oil. Purification by column chromatography (0-15% ethyl acetate in petroleum ether) gave methyl 6-(1-hydroxy-3-methylbutyl)nicotinate. 1H NMR (400 MHz, CDCl3, δ): 9.14 (s, 1H), 8.29-8.27 (d, 1H), 7.36-7.34 (d, 1H), 4.85-4.83 (m, 1H), 3.78 (s, 3H), 1.95-1.91 (m, 1H), 1.65-1.51 (m, 2H), 1.03-1.01 (d, 3H), 0.96-0.95 (d, 3H).

Workup

  1. stirringthe reaction was stirred at −10° C. for another 2 hours
  2. customThe reaction was quenched with water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to a brown oil
  7. customPurification by column chromatography (0-15% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-145097ea84d0449581c1e51f5c531c26
Source dataset
uspto-grants-2015_01
Patent number
US08933104B2

Reaction notes

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