[3-(1-Ethyl-1-methoxy-propyl)-pyridin-2-yl]-methanol → 3-(1-Ethyl-1-methoxy-propyl)-pyridine-2-carbaldehyde

HRID 1592426Notes

Reaction equation

HRID 1592426 reaction equation
[CH2:1]([C:3]([C:8]1[C:9]([CH2:14][OH:15])=[N:10][CH:11]=[CH:12][CH:13]=1)([O:6][CH3:7])[CH2:4][CH3:5])[CH3:2]>O=[Mn]=O.C(Cl)Cl>[CH2:1]([C:3]([C:8]1[C:9]([CH:14]=[O:15])=[N:10][CH:11]=[CH:12][CH:13]=1)([O:6][CH3:7])[CH2:4][CH3:5])[CH3:2]

Participants

4

Reactant 1

HCID 67272374[3-(1-Ethyl-1-methoxy-propyl)-pyridin-2-yl]-methanol

Product 1

HCID 865947603-(1-Ethyl-1-methoxy-propyl)-pyridine-2-carbaldehydeYield 46%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

Activated MnO2 (0.458 g, 5.26 mmol) was added to a stirred solution of [3-(1-ethyl-1-methoxy-propyl)-pyridin-2-yl]-methanol (0.110 g, 0.526 mmolbin CH2Cl2 (3 mL). The mixture was stirred for 16 h, and then filtered through a celite cake. The filtrate was concentrated by evaporation under vacuum, and the residue was purified by flash chromatography on a silica gel column (CH2Cl2), affording 3-(1-ethyl-1-methoxy-propyl)-pyridine-2-carbaldehyde as yellow oil (0.086 g, 46%). 1H NMR (CDCl3) δ 0.71 (t, 6H, J=7.5 Hz), 1.83-2.09 (m, 4H) 3.16 (s, 3H), 7.37 (dd, 1H, J=7.7, 4.8 Hz), 7.62 (dd, 1H, J=7.8, 1.5 Hz), 8.65 (dd, 1H, J=4.8, 1.5 Hz), 10.57 (s, 1H).

Workup

  1. filtrationfiltered through a celite cake
  2. concentrationThe filtrate was concentrated by evaporation under vacuum
  3. customthe residue was purified by flash chromatography on a silica gel column (CH2Cl2)

Sources & evidence

ORD record
ord-3a225f3dd8744721b8ed9ad98025487f
Source dataset
uspto-grants-2007_11
Patent number
US07291631B2

Reaction notes

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