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Water → (5-Diethoxyphosphoryloxyimino-5H-thiophen-2-ylidene)-(2-methylphenyl)-acetonitrile

HRID 1018889
ノート
印刷プレビュー

反応式

HRID 1018889 の反応式
[OH:1][N:2]=[C:3]1[S:7][C:6](=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])[C:9]#[N:10])[CH:5]=[CH:4]1.C([P:20](Cl)(CC)=[O:21])C.C(N([CH2:30][CH3:31])CC)C.[OH2:32].[O:33]1CC[CH2:35][CH2:34]1>>[CH2:34]([O:33][P:20]([O:1][N:2]=[C:3]1[S:7][C:6](=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])[C:9]#[N:10])[CH:5]=[CH:4]1)([O:21][CH2:30][CH3:31])=[O:32])[CH3:35]
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 5

HCID 962WaterHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 5195381Diethylphosphinoyl chlorideHCID 86758612HCID 86758612、化合物

生成物 1

HCID 53810703(5-Diethoxyphosphoryloxyimino-5H-thiophen-2-ylidene)-(2-methylphenyl)-acetonitrile

反応条件

温度
5 °C

実験手順

8 g (33 mmol) of (5-Hydroxyimino-5H-thiophen-2-ylidene)-(2-methylphenyl)-acetonitrile are dissolved in 90 ml of tetrahydrofuran (THF) and cooled in an ice bath. After adding 6.3 g (36 mmol) of diethylphosphoryl chloride to the solution, 5.0 g (50 mmol) of triethylamine are added dropwise, keeping the temperature below 50° C. The reaction mixture is stirred at 5° C. for 60 min., then poured into 100 ml of water, and extracted with ethyl acetate. The organic phase is washed with 0.1N hydrochloric acid solution, water, and sodium chloride solution. The organic phase is dried over MgSO4, the solvent is distilled off, and the residue is purified by flash chromatography on silica gel with ethyl acetate—hexane (1:1) as eluent. The product is obtained in the form of a yellow solid, melting point 90-91° C. The structure is confirmed by the 1H-NMR spectrum (CDCl3). δ [ppm]: 1.43 (t, 6H), 2.37 (s, 3H), 4.36-4.47 (m, 4H), 6.13 (d, 1H), 6.86 (d, 1H), 7.19-7.39 (m, 4H).

後処理

  1. temperaturecooled in an ice bath
  2. additionare added dropwise
  3. customthe temperature below 50° C
  4. extractionextracted with ethyl acetate
  5. washThe organic phase is washed with 0.1N hydrochloric acid solution, water, and sodium chloride solution
  6. dry with materialThe organic phase is dried over MgSO4
  7. distillationthe solvent is distilled off
  8. customthe residue is purified by flash chromatography on silica gel with ethyl acetate—hexane (1:1) as eluent
  9. customThe product is obtained in the form of a yellow solid, melting point 90-91° C

出典と根拠

ORDレコード
ord-93baef1de423460c9cf0587cecb58c3f
出典データセット
uspto-grants-2002_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06485886B1

反応ノート

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