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Triphenylphosphine → N-(6-Formyl-4-methylpyridin-2-YL)acetamide

HRID 505432
ノート
印刷プレビュー

反応式

HRID 505432 の反応式
[CH3:1][C:2]1[CH:7]=[C:6]([CH:8]=C)[N:5]=[C:4]([NH:10][C:11](=[O:13])[CH3:12])[CH:3]=1.[O:14]=[O+][O-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CO.ClCCl>[CH:8]([C:6]1[N:5]=[C:4]([NH:10][C:11](=[O:13])[CH3:12])[CH:3]=[C:2]([CH3:1])[CH:7]=1)=[O:14]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 11776TriphenylphosphineHCID 24823Ozone3 回HCID 68461930N-(4-Methyl-6-vinyl-pyridin-2-yl)-acetamide2 回

生成物 1

HCID 72214398N-(6-Formyl-4-methylpyridin-2-YL)acetamide

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
-80 °C

実験手順

5.0 g N-(4-methyl-6-vinyl-pyridin-2-yl)-acetamide (compound F5) are dissolved in a mixture of each 200 ml methanol and dichloromethane and cooled to −80° C. Subsequently, ozone is passed into the solution (flow 20-25 l/h ozone). After 5 min ozone treatment is stopped. Thereafter, nitrogen is applied for 5 min and 7.44 g of triphenylphosphane are added while stirring is continued. The solution is allowed to warm up to r.t. Subsequently, the volatile components are removed in vacuo and the residue is purified by chromatography on silica gel (eluent cyclohexane/ethyl acetate 3:1) to afford 2.72 g of the title compound as colourless solid. M.p. 202° C. GC-MS: 178.2 (M+). TLC: Rf=0.50 (cyclohexane/ethyl acetate 1:1). [Remark: Occasionally remaining traces of triphenylphosphine oxide can be removed by dissolving crude product in ethyl acetate followed by cooling to precipitate triphenylphosphine oxide.]

後処理

  1. temperatureto warm up to r.t
  2. customSubsequently, the volatile components are removed in vacuo
  3. customthe residue is purified by chromatography on silica gel (eluent cyclohexane/ethyl acetate 3:1)

出典と根拠

ORDレコード
ord-a4433b800bab4e53b6cb7cd884cc860b
出典データセット
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07781453B2

反応ノート

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