(4-Chloro-3-methyl-2-pyridyl)-cyclopropyl-methanol → (4-Chloro-3-methyl-2-pyridyl)cyclopropylketone

HRID 1854820Notes

Reaction equation

HRID 1854820 reaction equation
[CH3:1][C:2]1[C:3]([CH:9]([CH:11]2[CH2:13][CH2:12]2)[OH:10])=[N:4][CH:5]=[CH:6][C:7]=1[Cl:8]>ClCCl.O=[Mn]=O>[CH3:1][C:2]1[C:3]([C:9]([CH:11]2[CH2:13][CH2:12]2)=[O:10])=[N:4][CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 1

HCID 12071707(4-Chloro-3-methyl-2-pyridyl)-cyclopropyl-methanol

Product 1

HCID 66980317(4-Chloro-3-methyl-2-pyridyl)cyclopropylketoneYield 98.2%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of (3-methyl-4-chloro-pyridin-2-yl)-cyclopropyl-methanol (7.01 g, 35.5 mmol) in dichloromethane (80 mL) was treated with MnO2 (30.8 g, 355 mmol) at room temperature overnight. The reaction mixture was filtered through a pad of Celite and the filtrate was concentrated to dryness, affording the title compound (6.82 g, 98%). ESI-MS m/z: 196 (M+H)+; 1H NMR (CDCl3, 300 MHz) δ ppm: 8.41 (d, J=5.4 Hz, 1H), 7.42 (d, J=5.4 Hz, 1H), 2.96-3.04 (m, 1H), 2.57 (s, 3H), 1.20-1.28 (m, 2H), 1.14-1.09 (m, 2H).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite
  2. concentrationthe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-8cd13742107b4d80a6c801f8988b57b1
Source dataset
uspto-grants-2015_02
Patent number
US08962842B2

Reaction notes

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