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

HRID 1038060

반응식

HRID 1038060 반응식
[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]

참가 물질

5

반응물 3

HCID 69072Methyl 2-nitrobenzoateHCID 5884532-TrimethylsilylthiazoleHCID 178418339Butyllithium

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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)

후처리

  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)

출처 및 근거

ORD 기록
ord-7b2d61a9a6164f63acab9fac58946e09
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546404B2

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