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

HRID 1038060

Reaction equation

HRID 1038060 reaction equation
[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]

Participants

5

Reactant 3

HCID 69072Methyl 2-nitrobenzoateHCID 5884532-TrimethylsilylthiazoleHCID 178418339Butyllithium

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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)

Workup

  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)

Sources & evidence

ORD record
ord-7b2d61a9a6164f63acab9fac58946e09
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Linked notes

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