Potassium Carbonate → 780800-88-6

HRID 1592390Notes

Reaction equation

HRID 1592390 reaction equation
[CH2:1]([C:5]1[C:6]([CH3:12])=[N+:7]([O-])[CH:8]=[CH:9][CH:10]=1)[CH:2]([CH3:4])[CH3:3].C([O-])([O-])=[O:14].[K+].[K+]>CC(OC(C)=O)=O.CO>[CH2:1]([C:5]1[C:6]([CH2:12][OH:14])=[N:7][CH:8]=[CH:9][CH:10]=1)[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 67272106HCID 67272106, compound

Product 1

HCID 67272622780800-88-6

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
100 °C

Procedure

3-Isobutyl-2-methyl-pyridine-1-oxide (821 mg, 4.97 mmol) was dissolved in Ac2O (10 mL) and stirred at 100° C. for 16 hours. The Ac2O was removed under reduced pressure and the resulting brown oil was quenched with saturated NaHCO3 (30 mL) and extracted with CH2Cl2 (6×50 mL). The combined organic extracts were dried (Na2SO4), filtered, and concentrated in vacuo to yield a brown oil. Purification was avoided at this step due to the identical Rf values of the two products formed. The brown oil was dissolved in MeOH (20 mL) and powdered K2CO3 (2.05 g) was added. The mixture was stirred at room temperature for 2.5 hours. The solid was removed via suction filtration and the filtrate was concentrated in vacuo to give a brown oil. Purification via column chromatography on silica gel (CH2Cl2:MeOH, 95:5, v/v) afforded (3-isobutyl-pyridin-2-yl)-methanol as a yellow oil (383 mg, 78%, 2-steps). 1H NMR (CDCl3) δ 0.93 (d, 6H, J=6.0 Hz), 1.86 (m, 1H), 2.38 (d, 2H, J=6.0 Hz), 4.73 (s, 2H), 4.90 (br s, 1H), 7.18 (dd, 1H, J=9.0, 3.0 Hz), 7.45 (d, 1H, J=9.0), 8.41 (d, 1H, J=6.0 Hz).

Workup

  1. customThe Ac2O was removed under reduced pressure
  2. customthe resulting brown oil was quenched with saturated NaHCO3 (30 mL)
  3. extractionextracted with CH2Cl2 (6×50 mL)
  4. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto yield a brown oil
  8. customPurification
  9. customformed
  10. stirringThe mixture was stirred at room temperature for 2.5 hours
  11. customThe solid was removed via suction filtration
  12. concentrationthe filtrate was concentrated in vacuo
  13. customto give a brown oil
  14. customPurification via column chromatography on silica gel (CH2Cl2

Sources & evidence

ORD record
ord-758e76ecd9b34cec95a31cc22382c6b9
Source dataset
uspto-grants-2007_11
Patent number
US07291631B2

Reaction notes

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