Ethyl Acetate → 4-Tert-butyl-2-chloro-6-methylpyridine

HRID 1446719Notes

Reaction equation

HRID 1446719 reaction equation
P(Cl)(Cl)([Cl:3])=O.[C:6]([C:10]1[CH:15]=[CH:14][N+:13]([O-])=[C:12]([CH3:17])[CH:11]=1)([CH3:9])([CH3:8])[CH3:7].C(OCC)(=O)C>ClCCl>[Cl:3][C:14]1[CH:15]=[C:10]([C:6]([CH3:9])([CH3:8])[CH3:7])[CH:11]=[C:12]([CH3:17])[N:13]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 24813Phosphorus oxychlorideHCID 594853984-tert-Butyl-2-methyl-pyridine 1-oxide

Product 1

HCID 601265994-Tert-butyl-2-chloro-6-methylpyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

Add phosphorus oxychloride (15 mL) to 4-tert-butyl-2-methyl-pyridine 1-oxide (2.00 g, 12.10 mmol) and heat to 100° C. for 36 hours. Evaporate off the excess phosphorus oxychloride. Treat the oil cautiously with ice and water with stirring and make basic by treatment with aqueous bicarbonate solution. Extract with dichloromethane (3×75 mL) and pool, desiccate, filter, and concentrated. Chromatograph the crude product on silica using a gradient of (0→5→8%) ethyl acetate in dichloromethane to afford the title compound (0.82 g, 4.46 mmol). MS (ESI), m/z 184 (M+1).

Workup

  1. customEvaporate off the excess phosphorus oxychloride
  2. additionTreat the oil cautiously with ice and water
  3. extractionExtract with dichloromethane (3×75 mL) and pool, desiccate
  4. filtrationfilter
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2d263cae928d4b339bb7ec3c197b9b7c
Source dataset
uspto-grants-2010_02
Patent number
US07666879B2

Reaction notes

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