Methyl 2-nitrobenzoate → (2-Nitrophenyl)-(2-trimethylsilanylthiazol-5-yl)methanone

HRID 1038060

反応式

HRID 1038060 の反応式
[CH3:1][Si:2]([CH3:9])([CH3:8])[C:3]1[S:4][CH:5]=[CH:6][N:7]=1.[Li]CCCC.[N+:15]([C:18]1[CH:27]=[CH:26][CH:25]=[CH:24][C:19]=1[C:20](OC)=[O:21])([O-:17])=[O:16]>C1COCC1>[N+:15]([C:18]1[CH:27]=[CH:26][CH:25]=[CH:24][C:19]=1[C:20]([C:5]1[S:4][C:3]([Si:2]([CH3:9])([CH3:8])[CH3:1])=[N:7][CH:6]=1)=[O:21])([O-:17])=[O:16]

参加物

5

反応物 3

HCID 69072Methyl 2-nitrobenzoateHCID 5884532-TrimethylsilylthiazoleHCID 178418339Butyllithium

生成物 1

HCID 57686181(2-Nitrophenyl)-(2-trimethylsilanylthiazol-5-yl)methanone

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 2-trimethylsilylthiazole (2.0 g, 12.7 mmol) in THF at −78 C was added BuLi (5.08 mL, 2.5 M, 12.7 mmol). The reaction was stirred at −78 C for 0.5 hr and methyl 2-nitrobenzoate (2.69 mL, 19.1 mmol) was added. The suspension was stirred at room temperature for 2 hr and quenched with ammonium chloride solution. The mixture was extracted with ethyl acetate and the combined organic layer was dried over sodium sulfate, concentrated and purified by column chromatography to give 2H (680 mg)

後処理

  1. stirringThe suspension was stirred at room temperature for 2 hr
  2. customquenched with ammonium chloride solution
  3. extractionThe mixture was extracted with ethyl acetate
  4. dry with materialthe combined organic layer was dried over sodium sulfate
  5. concentrationconcentrated
  6. custompurified by column chromatography
  7. customto give 2H (680 mg)

出典と根拠

ORDレコード
ord-7b2d61a9a6164f63acab9fac58946e09
出典データセット
uspto-grants-2013_10
特許番号
US08546404B2

関連ノート

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