Sodium amide → HCID 10026043, compound

HRID 1087294Notes

Reaction equation

HRID 1087294 reaction equation
[NH2-].[Na+].CCOC(C(P(OCC)(OCC)=O)C)=O.C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)N2C=C(C(=O)C)N=C2)C=CC=CC=1.[CH3:45]/[C:46](=[C:52](\[C:54]1[N:55]=[CH:56][N:57]([C:59]([C:72]2[CH:77]=[CH:76][CH:75]=[CH:74][CH:73]=2)([C:66]2[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=2)[C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=2)[CH:58]=1)/[CH3:53])/[C:47]([O:49][CH2:50][CH3:51])=[O:48]>O1CCCC1.C(OCC)C>[CH3:45]/[C:46](=[C:52](/[C:54]1[N:55]=[CH:56][N:57]([C:59]([C:72]2[CH:77]=[CH:76][CH:75]=[CH:74][CH:73]=2)([C:66]2[CH:67]=[CH:68][CH:69]=[CH:70][CH:71]=2)[C:60]2[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=2)[CH:58]=1)\[CH3:53])/[C:47]([O:49][CH2:50][CH3:51])=[O:48]

Participants

7

Reactant 4

HCID 24533Sodium amideHCID 107155Triethyl 2-phosphonopropionateHCID 10071717HCID 10071717, compoundHCID 104280901-(1-trityl-1H-imidazol-4-yl)ethanone

Product 1

HCID 10026043HCID 10026043, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

11.7 g (0.3 mol) sodium amide are suspended in 300 ml tetrahydrofurane under nitrogene. 71.47 g (0.3 mol) triethyl 2-phosphonopropionate are dropped to the stirred mixture which is kept at ambient temperature for 2 hours subsequently. 30.5 g (86.5 mmol) 1-(1-triphenylmethyl-1H-imidazol-4-yl)ethanone are added and the mixture is held under reflux for 16 hours. Evaporation and dissolving in 1 l chloroform/2-propanol (3:1) is follwed by washing 3 times with water. Drying with sodium sulphate and evaporation result an oil which mainly consists of E-ethyl 2-methyl-3-(1-triphenylmethyl-1H-imidazol-4-yl)2-butenate. Treating this residue with diethyl ether affords 10.9 g of a solid material mainly consisting of the Z-isomer. Purification via column chromatography (silicagel 63-200 μm, eluent: petrol ether/diethyl ether [2:2]) leads to 5.6 g (14.8%) of the title compound as a white solid. An analytical sample was recrystallized from diethyl ether/ethanol resulting colourless crystals, melting point 166°-168° C.

Workup

  1. temperatureunder reflux for 16 hours
  2. customEvaporation
  3. dissolutiondissolving in 1 l chloroform/2-propanol (3:1)
  4. washby washing 3 times with water
  5. dry with materialDrying with sodium sulphate and evaporation
  6. customresult an oil which

Sources & evidence

ORD record
ord-746fb335de4140748c2abf14b4f0e3b6
Source dataset
uspto-grants-1991_07
Patent number
US05034539

Reaction notes

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