(3-(Benzyloxy)pyridin-2-yl)methanol → 3-(Benzyloxy)pyridine-2-carbaldehyde

HRID 712473Notes

Reaction equation

HRID 712473 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([CH2:15][OH:16])=[N:11][CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(Cl)(Cl)Cl.O=[Mn]=O>[CH2:1]([O:8][C:9]1[C:10]([CH:15]=[O:16])=[N:11][CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 13217540(3-(Benzyloxy)pyridin-2-yl)methanol

Product 1

HCID 133745943-(Benzyloxy)pyridine-2-carbaldehydeYield 73%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6212ChloroformSolvent

Procedure

A mixture of (3-(benzyloxy)pyridin-2-yl)methanol (7.50 g) and MnO2 (30.00 g) in CHCl3 was heated to reflux for 90 min, and then cooled to rt. The reaction mixture was filtered. The filtrate was concentrated in vacuo and the residue was chromatographed with a silica gel column (eluting agent: 2:1 (v/v) PE/EA) to give the title compound as a pale yellow solid (5.40 g, 73.00%), HPLC: 93.00%. The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 214.6 (M+1); 1H NMR (400 MHz, CDCl3) δ: 5.26 (s, 2H), 7.34-7.47 (m, 7H), 8.41 (t, J=2.5 Hz, 1H), 10.40 (s, 1H) ppm.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 90 min
  3. filtrationThe reaction mixture was filtered
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue was chromatographed with a silica gel column (eluting agent: 2:1 (v/v) PE/EA)

Sources & evidence

ORD record
ord-4c8eaba5fa614573b6f506ddc137659e
Source dataset
uspto-grants-2015_11
Patent number
US09181277B2

Reaction notes

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