Sodium Bicarbonate → HCID 12691759, compound

HRID 2070943Notes

Reaction equation

HRID 2070943 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6]([CH3:15])=[N:7][C:8]([CH3:14])=[C:9]([CH:13]=1)[C:10](O)=[O:11])=[O:4].B.C1COCC1.CC(O)=O.O.C([O-])(O)=O.[Na+]>C1COCC1.O.CCOC(C)=O>[OH:11][CH2:10][C:9]1[C:8]([CH3:14])=[N:7][C:6]([CH3:15])=[C:5]([CH:13]=1)[C:3]([O:2][CH3:1])=[O:4]

Participants

8

Reactant 4

HCID 516892Sodium BicarbonateHCID 2723981Borane;tetrahydrofuranHCID 21899381Acetic acid--water (1/1)HCID 68669960HCID 68669960, compound

Product 1

HCID 12691759HCID 12691759, compoundYield 71%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 686 mg of 5-(methoxycarbonyl)-2,6-dimethylnicotinic acid and 8.0 mL of BH3.THF (1.0 M in THF) in 10 mL of THF was heated to 75° C. for 2.5 h. An aqueous solution of 3 mL of AcOH:H2O (1:1) was added, and the solution was stirred until the bubbling ceased. Saturated NaHCO3 was added to a pH=7, and the solution was stirred overnight. EtOAc and H2O were added, and the layers were separated. The aqueous layer was extracted with 30 mL of EtOAc, and the combined extracts were washed with brine, dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography (3% MeOH/CHCl3) provided 452 mg of methyl 5-(hydroxymethyl)-2,6-dimethylnicotinate as a pale yellow solid in 71% yield.

Workup

  1. stirringthe solution was stirred overnight
  2. customthe layers were separated
  3. extractionThe aqueous layer was extracted with 30 mL of EtOAc
  4. washthe combined extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by flash silica gel chromatography (3% MeOH/CHCl3)

Sources & evidence

ORD record
ord-fdcb80b732804d80b3fd598f5009640b
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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