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

HRID 579935노트

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HRID 579935 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
31 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ba1e72e644114016b4babeb274fbd25b
출처 데이터셋
uspto-grants-1988_06
특허 번호
US04751163

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