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

HRID 1394560ノート

反応式

HRID 1394560 の反応式
[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

参加物

5

反応物 2

HCID 167693TrimethylsilyldiazomethaneHCID 22270370HCID 22270370、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-f0ea95170b1b4d1abff73c995ca404c7
出典データセット
uspto-grants-2008_03
特許番号
US07348456B2

反応ノート

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