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

HRID 1394560노트

반응식

HRID 1394560 반응식
[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

참가 물질

5

반응물 2

HCID 167693TrimethylsilyldiazomethaneHCID 22270370HCID 22270370, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-f0ea95170b1b4d1abff73c995ca404c7
출처 데이터셋
uspto-grants-2008_03
특허 번호
US07348456B2

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