Dichloromethane methanol → 5-Chloro-6-ethyl-3-pyridinecarbaldehyde

HRID 420733Notes

Reaction equation

HRID 420733 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:10][OH:11])[CH:5]=[N:6][C:7]=1[CH2:8][CH3:9].C(Cl)Cl.CO>C(Cl)Cl.O=[Mn]=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[O:11])[CH:5]=[N:6][C:7]=1[CH2:8][CH3:9]

Participants

5

Reactant 2

HCID 21226129Dichloromethane methanolHCID 59698822(5-Chloro-6-ethyl-3-pyridinyl)methanol

Product 1

HCID 580017515-Chloro-6-ethyl-3-pyridinecarbaldehydeYield 51.1%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

MnO2 (620 mg, 7.13 mmol) was added to a solution of (5-chloro-6-ethyl-3-pyridinyl)methanol (103 mg, 0.600 mmol) in DCM (4 ml) and the mixture was stirred at room temperature overnight. TLC (10% DCM/MeOH) showed starting material remaining. An excess of MnO2 (261 mg, 3.00 mmol) was added. After stirring for 3 h, the reaction went to completion. The resulting suspension was filtered and washed with DCM. The filtrate was concentrated under reduced pressure to give 52 mg of the title compound as colourless oil.

Workup

  1. stirringAfter stirring for 3 h
  2. filtrationThe resulting suspension was filtered
  3. washwashed with DCM
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-657aa11c157843188b904679fa3e189a
Source dataset
uspto-grants-2012_01
Patent number
US08097628B2

Reaction notes

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