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

HRID 579935Notes

Reaction equation

HRID 579935 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
31 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-ba1e72e644114016b4babeb274fbd25b
Source dataset
uspto-grants-1988_06
Patent number
US04751163

Reaction notes

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