Acetic Anhydride → (6-Cyano-3-methyl-2-pyridinyl)methyl acetate

HRID 2356626ノート

反応式

HRID 2356626 の反応式
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].[CH3:8][C:9]1C(C)=[N+:13]([O-])[C:12]([C:17]#[N:18])=[CH:11][CH:10]=1.C(=O)(O)[O-].[Na+]>>[C:5]([O:4][CH2:1][C:2]1[C:9]([CH3:8])=[CH:10][CH:11]=[C:12]([C:17]#[N:18])[N:13]=1)(=[O:7])[CH3:6]

参加物

4

反応物 3

HCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 68455695HCID 68455695、化合物

生成物 1

HCID 68457478(6-Cyano-3-methyl-2-pyridinyl)methyl acetate収率 67%

反応条件

温度
120 °C

実験手順

To acetic anhydride (12 ml) at 120° C. was added 5,6-dimethyl-2-pyridine-carbonitrile 1-oxide (3.02 g) and the solution heated at 120° C. for 5 minutes then under reflux for 2.5 hours. After cooling the solution was added to ice (ca. 80 g) and the mixture neutralized with sodium bicarbonate. It was extracted with ether (80 ml then 2×40 ml) and the combined extracts washed with brine (40 ml), dried (MgSO4) and concentrated in vacuo. The residue was purified by Biotage chromatography eluting with 2:1 hexane:ethyl acetate to afford the title compound (2.60 g, 67%) as a pale yellow solid. LC/MS [MH+]=191, RT=2.05 min.

後処理

  1. temperatureunder reflux for 2.5 hours
  2. temperatureAfter cooling the solution
  3. extractionIt was extracted with ether (80 ml
  4. wash2×40 ml) and the combined extracts washed with brine (40 ml)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by Biotage chromatography
  8. washeluting with 2:1 hexane

出典と根拠

ORDレコード
ord-e3f3ca37c7db45c4af1c05e45434686f
出典データセット
uspto-grants-2010_07
特許番号
US07759369B2

反応ノート

読み込み中…