Dichloromethane → 2-(Chloromethyl)-5-ethylpyridine

HRID 892191Notes

Reaction equation

HRID 892191 reaction equation
[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH3:10])=[N+:7]([O-])[CH:8]=1)[CH3:2].C(N(CC)CC)C.C(Cl)[Cl:19]>CCOC(C)=O>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:10][Cl:19])=[N:7][CH:8]=1)[CH3:2]

Participants

5

Reactant 3

HCID 6344Dichloromethane3×HCID 8471TriethylamineHCID 698505-Ethyl-2-methylpyridine 1-oxide

Product 1

HCID 157171792-(Chloromethyl)-5-ethylpyridine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 5-ethyl-2-methyl-pyridine-1-oxide (427 mg, 3.11 mmol, example 45c) in CH2Cl2 (2 mL) is added a solution (0.2 mL) of phosphorous (v) trichloride oxide (327 μL) in CH2Cl2 (2 mL). Added simultaneously the remaining phosphorous (v) trichloride oxide solution and a solution of triethylamine (488 μL) in CH2Cl2 (2 mL) at such a rate as to maintain a reflux. After the addition is complete, let reaction mixture cool to 20° C. and diluted with EtOAc. The organic layer is washed with sat. NaHCO3 soln., brine, dried over MgSO4 and concentrated. The residue is purified by flash chromatography (silica, 10% ethyl acetate in dichloromethane) to provide the title compound. MS (ESI) 156 (M+H)+.

Workup

  1. additionAfter the addition
  2. customreaction mixture
  3. washThe organic layer is washed with sat. NaHCO3 soln
  4. dry with material, brine, dried over MgSO4
  5. concentrationconcentrated
  6. customThe residue is purified by flash chromatography (silica, 10% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-22ec18a436444917a7040ef396453f94
Source dataset
uspto-grants-2006_02
Patent number
US07005440B1

Reaction notes

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