Sodium hydride → Tert-butyl[(3-bromo-5-chloropyridin-2-yl)oxy]acetate

HRID 2390240ノート

反応式

HRID 2390240 の反応式
[CH3:1][C:2]([O:5][C:6]([CH2:8][OH:9])=[O:7])([CH3:4])[CH3:3].[H-].[Na+].[Br:12][C:13]1[C:14](Cl)=[N:15][CH:16]=[C:17]([Cl:19])[CH:18]=1>C1COCC1>[C:2]([O:5][C:6](=[O:7])[CH2:8][O:9][C:14]1[C:13]([Br:12])=[CH:18][C:17]([Cl:19])=[CH:16][N:15]=1)([CH3:4])([CH3:3])[CH3:1]

参加物

5

反応物 3

HCID 24758Sodium hydride2 回HCID 11815394Tert-butyl 2-hydroxyacetate2 回HCID 129015963-Bromo-2,5-dichloropyridine

生成物 1

HCID 58521889Tert-butyl[(3-bromo-5-chloropyridin-2-yl)oxy]acetate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

A solution of 2-tert-butyl glycolate (437 mg; 3.31 mmol) in anhydrous THF (5 mL) was treated with NaH (159 mg; 3.97 mmol) and stirred at RT for 10 minutes before treating with a solution of 3-bromo-2,5-dichloropyridine (Matrix; 500 mg; 2.20 mmol) in anhydrous THF (5 mL). The resulting reaction mixture was stirred for 22 hours. The reaction mixture was treated with a solution of 2-tert-butyl glycolate (437 mg; 3.31 mmol) in THF (2 ml), then with NaH (159 mg; 3.97 mmol) and the reaction mixture was stirred for 16 h. The reaction was quenched with tBuOH, the solvent removed under reduced pressure affording a brown solid, which was purified by flash column chromatography (silica), eluting with cyclohexane containing increasing amounts of EtOAc, affording the title compound as a yellow sticky solid.

後処理

  1. customThe resulting reaction mixture
  2. stirringwas stirred for 22 hours
  3. customThe reaction was quenched with tBuOH
  4. customthe solvent removed under reduced pressure
  5. customaffording a brown solid, which
  6. customwas purified by flash column chromatography (silica)
  7. washeluting with cyclohexane containing
  8. temperatureincreasing amounts of EtOAc

出典と根拠

ORDレコード
ord-6652785368514f6cb8ed87741996c671
出典データセット
uspto-grants-2012_09
特許番号
US08273769B2

反応ノート

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