780800-88-6 → HCID 86594752, compound

HRID 250953Notes

Reaction equation

HRID 250953 reaction equation
[CH2:1]([C:5]1[C:6]([CH2:11][OH:12])=[N:7][CH:8]=[CH:9][CH:10]=1)[CH:2]([CH3:4])[CH3:3]>C(Cl)Cl.O=[Mn]=O>[CH2:1]([C:5]1[C:6]([CH:11]=[O:12])=[N:7][CH:8]=[CH:9][CH:10]=1)[CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 1

HCID 67272622780800-88-6

Product 1

HCID 86594752HCID 86594752, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

MnO2 (2.01 g, 23.2 mmol) was added to a flask containing a solution of (3-isobutyl-pyridin-2-yl)-methanol (383 mg, 2.32 mmol) in CH2Cl2 (15 mL). The black mixture was stirred at room temperature for 22 hours and then filtered through celite. The filtrate was concentrated in vacuo to give a yellow oil. Purification via column chromatography on silica gel (CH2Cl2:MeOH, 97.5:2.5, v/v) afforded 3-isobutyl-pyridine-2-carbaldehyde as an orange oil (344 mg, 91%). 1H NMR (CDCl3) δ 0.93 (d, 6H, J=6.0 Hz), 1.87 (m, 1H), 2.94 (d, 2H, J=6.0 Hz), 7.39 (dd, 1H, J=9.0, 3.0 Hz), 7.60 (d, 1H, J=9.0), 8.67 (d, 1H, J=6.0 Hz), 10.18 (s, 1H).

Workup

  1. filtrationfiltered through celite
  2. concentrationThe filtrate was concentrated in vacuo
  3. customto give a yellow oil
  4. customPurification via column chromatography on silica gel (CH2Cl2

Sources & evidence

ORD record
ord-b20e34de24f646e7b3687d0609b19e55
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

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