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

HRID 1987290Notes

Reaction equation

HRID 1987290 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.[CH2:17](Cl)Cl>CO.CCCCCC>[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 6344DichloromethaneHCID 22270370HCID 22270370, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8058HexaneSolvent

Procedure

To a solution of 2-(4-trifluoromethyl-2-pyridyloxy)propionic acid (Step A, 15 g, 55 mol) in 100 mL CH2Cl2 and 100 mL MeOH at 0° C. was added trimethylsilydiazomethane (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% EtOAc in hexane to give methyl 2-(4-trifluoromethyl-2-pyridyloxy)propionate (10 g), which was used immediately for methylation following the procedure described in Reference Example 39, 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% EtOAc in hexane

Sources & evidence

ORD record
ord-fba902d574324552814629e4794e1754
Source dataset
uspto-grants-2009_06
Patent number
US07550489B2

Reaction notes

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