Trimethylsilyldiazomethane → Methyl 2-(4-trifluoromethyl-2-pyridyloxy)propionate

HRID 2104279Notes

Reaction equation

HRID 2104279 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:8]=[CH:7][N:6]=[C:5]([O:9][CH:10]([CH3:14])[C:11]([OH:13])=[O:12])[CH:4]=1.[CH3:17][Si](C=[N+]=[N-])(C)C>C(Cl)Cl.CO>[F:16][C:2]([F:15])([F:1])[C:3]1[CH:8]=[CH:7][N:6]=[C:5]([O:9][CH:10]([CH3:14])[C:11]([O:13][CH3:17])=[O:12])[CH:4]=1

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 22270370HCID 22270370, compound

Product 1

HCID 22270664Methyl 2-(4-trifluoromethyl-2-pyridyloxy)propionate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4-trifluoromethyl-2-pyridyloxy)propionic acid (Step A, 15 g, 55 mol) in 100 mL of methylene chloride and 100 mL of methanol at 0° C. was added trimethylsilyldiazomethane (2 M solution in hexane) until a yellow color persisted. After stirring at room temperature for 15 min, the reaction mixture was concentrated to dryness, and the residue was purified by flash chromatography on silica gel eluted with 0 to 10% ethyl acetate in hexane to give methyl 2-(4-trifluoromethyl-2-pyridyloxy)propionate, which was used immediately for methylation following the procedure described in Reference Example 13, Step B substituting ethyl iodide with methyl iodide. 1H NMR (500 MHz, CD3OD): δ 8.25 (d, 1H), 7.18 (d, 1H), 7.15 (s, 1H), 3.65 (s, 3H), 1.65 (s, 6H).

Workup

  1. concentrationthe reaction mixture was concentrated to dryness
  2. customthe residue was purified by flash chromatography on silica gel
  3. washeluted with 0 to 10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-94b66f6c244544428dcb417e03d980f6
Source dataset
uspto-grants-2009_08
Patent number
US07576239B2

Reaction notes

Loading…