3-Phenylpyridine → 2-Methyl-5-phenylpyridine

HRID 892221

反応式

HRID 892221 の反応式
[C:1]1([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:13][Li]>C(OCC)C>[C:1]1([C:7]2[CH:12]=[CH:11][C:10]([CH3:13])=[N:9][CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

4

反応物 2

HCID 138863-PhenylpyridineHCID 178418348HCID 178418348、化合物

生成物 1

HCID 767442-Methyl-5-phenylpyridine

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

To a cooled (−70° C.) solution of 3-phenylpyridine (1.43 mL, 10.0 mmoles) in diethyl ether (7.5 mL) is added dropwise methyllithium (LiBr complex, 1.5 M in diethyl ether, 7.33 mL, 11.0 mmoles). After letting warm to room temperature over 16 hours the reaction is cooled (0° C.) and quenched with distilled water (5 mL). The reaction is then extracted with methylene chloride, the organic layer isolated and concentrated, and the resulting residue purified by column chromatography (silica, 3:1 hexane: EtOAc) to yield the title compound as a pale yellow oil. MS(ESI) 170 (M+H)+.

後処理

  1. temperatureis cooled (0° C.)
  2. customquenched with distilled water (5 mL)
  3. extractionThe reaction is then extracted with methylene chloride
  4. customthe organic layer isolated
  5. concentrationconcentrated
  6. customthe resulting residue purified by column chromatography (silica, 3:1 hexane: EtOAc)

出典と根拠

ORDレコード
ord-9f391ccfc2a144e1b9db62899f3d1216
出典データセット
uspto-grants-2006_02
特許番号
US07005440B1

関連ノート

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