(2-Chloro-6-methoxypyridin-4-yl)methanol → 2-Chloro-6-methoxypyridine-4-carbaldehyde
Reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][OH:9])[CH:5]=[C:4]([O:10][CH3:11])[N:3]=1.C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>C(Cl)Cl.CCOCC>[Cl:1][C:2]1[CH:7]=[C:6]([CH:5]=[C:4]([O:10][CH3:11])[N:3]=1)[CH:8]=[O:9]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of (2-chloro-6-methoxypyridin-4-yl)methanol (1.73 g, 9.97 mmole) from the protocol immediately above in CH2Cl2 (40 mL) was added PCC (2.58 g, 11.96 mmole) all at once at RT. After 60 hr the mixture was diluted with Et2O and filtered through a plug of Celite®. The filtrate was concentrated to give the titled compound as a tan-yellow solid which was sufficiently pure for use in the next step. 1H-NMR (500 MHz, CDCl3) δ 9.96 (s, 1 H), 7.32 (s, 1 H), 7.06 (s, 1 H), 4.00 (s, 3 H).