Diethyl benzhydrylphosphonate → 1-(4-Diethylaminophenyl)-1,4,4-triphenyl-1,3-butadiene

HRID 579935ノート

反応式

HRID 579935 の反応式
[CH2:1]([N:3]([CH2:20][CH3:21])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:11][CH:12]=O)=[CH:6][CH:5]=1)[CH3:2].[C:22]1([CH:28](P(=O)(OCC)OCC)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.CC(C)([O-])C.[K+]>CN(C=O)C>[CH2:1]([N:3]([CH2:20][CH3:21])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:11][CH:12]=[C:28]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:6][CH:5]=1)[CH3:2]

参加物

5

反応物 3

HCID 10267017Diethyl benzhydrylphosphonateHCID 23665647Potassium tert-butoxideHCID 542012503-(p-Diethylaminophenyl)-3-phenylacrolein

生成物 1

HCID 534221431-(4-Diethylaminophenyl)-1,4,4-triphenyl-1,3-butadiene収率 68%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
31 °C

実験手順

2.79 g of 3-(p-diethylaminophenyl)-3-phenylacrolein and 3.34 g of diethyl diphenylmethylphosphonate were dissolved in 100 ml of DMF, and 1.23 g of potassium t-butoxide was added thereto at room temperature. The temperature of the reaction mixture was increased to 31° C. by a heat generated and, thereafter, the reaction was conducted at room temperature for 4 hours. The reaction mixture was poured into 100 cc of ice water and stirred. Deposited crystals were collected by filtration, dissolved in benzene, and separated and purified on silica gel column chromatography. After distilling off benzene from the eluate, the purified product was recrystallized from ethyl acetate to obtain 2.9 g (yield: 68% (theory)) of a pale-yellow crystal. m.p.: 124°-5° C.

後処理

  1. customat room temperature
  2. filtrationDeposited crystals were collected by filtration
  3. dissolutiondissolved in benzene
  4. customseparated
  5. custompurified on silica gel column chromatography
  6. distillationAfter distilling off benzene from the eluate
  7. customthe purified product was recrystallized from ethyl acetate
  8. customto obtain 2.9 g (yield: 68% (theory)) of a pale-yellow crystal

出典と根拠

ORDレコード
ord-ba1e72e644114016b4babeb274fbd25b
出典データセット
uspto-grants-1988_06
特許番号
US04751163

反応ノート

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