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

HRID 1355471Notes

Reaction equation

HRID 1355471 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) δ9.96 (s, 1H), 7.32 (s, 1H), 7.06 (s, 1H), 4.00 (s, 3H).

Workup

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

Sources & evidence

ORD record
ord-d6292a28800643dc941ebe6fcadcc399
Source dataset
uspto-grants-2003_07
Patent number
US06586423B2

Reaction notes

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