Hydrochloric Acid → 3-Nitrostilbene

HRID 2086772ノート

反応式

HRID 2086772 の反応式
[H-].[Na+].[CH2:3](P(=O)(OCC)OCC)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[N+:18]([C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH:24]=O)([O-:20])=[O:19].Cl>CN(C)C=O>[N+:18]([C:21]1[CH:22]=[C:23](/[CH:24]=[CH:3]/[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:26]=[CH:27][CH:28]=1)([O-:20])=[O:19]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 74493-NitrobenzaldehydeHCID 14122Diethyl benzylphosphonateHCID 24758Sodium hydride

生成物 1

HCID 9775603-Nitrostilbene収率 52.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

To a suspension of sodium hydride (60% in oil, 1.48 g) in N,N-dimethylformamide (40 ml) was added a solution of diethyl benzylphosphonate (7.69 g) in N,N-dimethylformamide (40 ml) at 0° C. The mixture was stirred at room temperature for 30 minutes, then a solution of 3-nitrobenzaldehyde (5.09 g) was added thereto. After stirring at 50° C. for 1 hour, the mixture was poured into dilute hydrochloric acid, and extracted with ethyl acetate 3 times. The combined organic solution was washed with water and brine, dried over magnesium sulfate and concentrated. The resultant solid was collected and washed with isopropyl ether to give (E)-3-nitrostilbene (3.97 g).

後処理

  1. stirringAfter stirring at 50° C. for 1 hour
  2. extractionextracted with ethyl acetate 3 times
  3. washThe combined organic solution was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe resultant solid was collected
  7. washwashed with isopropyl ether

出典と根拠

ORDレコード
ord-bf31108c068348599048d8e61d2be56c
出典データセット
uspto-grants-2004_04
特許番号
US06727245B2

反応ノート

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