(3-Isopropylpyridin-2-YL)methanol → 3-Isopropylpicolinaldehyde

HRID 1592379Notes

Reaction equation

HRID 1592379 reaction equation
[CH:1]([C:4]1[C:5]([CH2:10][OH:11])=[N:6][CH:7]=[CH:8][CH:9]=1)([CH3:3])[CH3:2]>C(Cl)Cl.[O-2].[Mn+4].[O-2]>[CH:1]([C:4]1[C:5]([CH:10]=[O:11])=[N:6][CH:7]=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 45091733(3-Isopropylpyridin-2-YL)methanol

Product 1

HCID 450836353-IsopropylpicolinaldehydeYield 61.7%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a vigorously stirred solution of (3-isopropyl-pyridin-2-yl)-methanol (26 g, 170 mmol) in CH2Cl2 (575 mL) was added manganese(IV) oxide (105 g, 1.20 mol) under N2. The mixture was stirred for 18 h then filtered through a celite pad and concentrated in vacuo. Purification by column chromatography on silica gel (EtOAc/hexanes, 1:3) afforded 3-isopropyl-pyridine-2-carbaldehyde (15.65 g, 61%) as an orange oil. 1H NMR (CDCl3) δ 1.26 (d, 6H, J=7.0 Hz), 4.17 (sep, 1H, J=6.6 Hz) 7.45 (dd, 1H, J=7.9, 4.4 Hz), 7.84 (d, 1H, J=7.9 Hz), 8.56 (dd, 1H, J=4.4, 1.3 Hz), 10.2 (s, 1H).

Workup

  1. filtrationthen filtered through a celite pad
  2. concentrationconcentrated in vacuo
  3. customPurification by column chromatography on silica gel (EtOAc/hexanes, 1:3)

Sources & evidence

ORD record
ord-19be94b0a8cb4c9295c353be1d16dc06
Source dataset
uspto-grants-2007_11
Patent number
US07291631B2

Reaction notes

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