Ethyl Acetate → 4-Tert-butyl-2-chloro-6-methylpyridine

HRID 1446719ノート

反応式

HRID 1446719 の反応式
P(Cl)(Cl)([Cl:3])=O.[C:6]([C:10]1[CH:15]=[CH:14][N+:13]([O-])=[C:12]([CH3:17])[CH:11]=1)([CH3:9])([CH3:8])[CH3:7].C(OCC)(=O)C>ClCCl>[Cl:3][C:14]1[CH:15]=[C:10]([C:6]([CH3:9])([CH3:8])[CH3:7])[CH:11]=[C:12]([CH3:17])[N:13]=1

参加物

5

反応物 3

HCID 8857Ethyl AcetateHCID 24813Phosphorus oxychlorideHCID 594853984-tert-Butyl-2-methyl-pyridine 1-oxide

生成物 1

HCID 601265994-Tert-butyl-2-chloro-6-methylpyridine

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
100 °C

実験手順

Add phosphorus oxychloride (15 mL) to 4-tert-butyl-2-methyl-pyridine 1-oxide (2.00 g, 12.10 mmol) and heat to 100° C. for 36 hours. Evaporate off the excess phosphorus oxychloride. Treat the oil cautiously with ice and water with stirring and make basic by treatment with aqueous bicarbonate solution. Extract with dichloromethane (3×75 mL) and pool, desiccate, filter, and concentrated. Chromatograph the crude product on silica using a gradient of (0→5→8%) ethyl acetate in dichloromethane to afford the title compound (0.82 g, 4.46 mmol). MS (ESI), m/z 184 (M+1).

後処理

  1. customEvaporate off the excess phosphorus oxychloride
  2. additionTreat the oil cautiously with ice and water
  3. extractionExtract with dichloromethane (3×75 mL) and pool, desiccate
  4. filtrationfilter
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-2d263cae928d4b339bb7ec3c197b9b7c
出典データセット
uspto-grants-2010_02
特許番号
US07666879B2

反応ノート

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