(2-Chloro-6-methoxypyridin-4-yl)methanol → 2-Chloro-6-methoxypyridine-4-carbaldehyde

HRID 1355534Notes

Reaction equation

HRID 1355534 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

HCID 11457961(2-Chloro-6-methoxypyridin-4-yl)methanolHCID 178418287HCID 178418287, compound

Product 1

HCID 27629762-Chloro-6-methoxypyridine-4-carbaldehyde

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

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).

Workup

  1. filtrationfiltered through a plug of Celite®
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-553b57b97ac6411eabc6f77ea68f8657
Source dataset
uspto-grants-2003_07
Patent number
US06586424B2

Reaction notes

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