Water → 4-(N-4-hydroxybutyl-N-butylamino)-4'-triflyl 1,4-diphenyl-1,3-butadiene

HRID 6205Notes

Reaction equation

HRID 6205 reaction equation
[Br-].[S:2]([C:9]1[CH:34]=[CH:33][C:12]([CH2:13][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:11][CH:10]=1)([C:5]([F:8])([F:7])[F:6])(=[O:4])=[O:3].[Li][CH2:36][CH2:37][CH2:38][CH3:39].[OH:40][CH2:41][CH2:42][CH2:43][CH2:44][N:45](C1C=CC(C=CC=O)=CC=1)[CH2:46][CH2:47][CH2:48][CH3:49].O>C1(C)C=CC=CC=1>[OH:40][CH2:41][CH2:42][CH2:43][CH2:44][N:45]([C:13]([C:12]1[CH:11]=[CH:10][C:9]([S:2]([C:5]([F:6])([F:7])[F:8])(=[O:3])=[O:4])=[CH:34][CH:33]=1)=[CH:39][CH:38]=[CH:37][C:36]1[CH:33]=[CH:34][CH:9]=[CH:10][CH:11]=1)[CH2:46][CH2:47][CH2:48][CH3:49]

Participants

6

Reactant 4

HCID 962WaterHCID 197950884-Triflylbenzyltriphenylphosphonium bromideHCID 539973884-(N-4-hydroxybutyl-N-butylamino)cinnamaldehydeHCID 178418339Butyllithium

Product 1

HCID 867472434-(N-4-hydroxybutyl-N-butylamino)-4'-triflyl 1,4-diphenyl-1,3-butadiene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a stirred solution of 110 g (0.2 mole) of 4-triflylbenzyltriphenylphosphonium bromide in toluene is added dropwise 0.2 moles of n-BuLi at room temperature. After 2 hours a solution of 27.5 g (0.1 mole) of 4[N-4-hydroxybutyl-N-butylamino]cinnamaldehyde in toluene is added dropwise to the mixture, and the reaction is stirred for 18 hours at room temperature. Water is added, and compound C is isolated by vacuum filtration, washed with 60% ethanol/water, dried under vacuum, and purified by recrystallization from ethanol.

Sources & evidence

ORD record
ord-d48d928ccbcc4d238b26df05d712c5e6
Source dataset
uspto-grants-1993_09
Patent number
US05247042

Reaction notes

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