Triethyl phosphite → Diethyl 7-(2,4,5-triphenylimidazol-1-yl)heptane-phosphonate

HRID 265395Notes

Reaction equation

HRID 265395 reaction equation
[C:1]1([C:7]2[N:8]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]Br)[C:9]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[P:32]([O:39]CC)([O:36][CH2:37][CH3:38])[O:33][CH2:34][CH3:35]>C1(C)C(C)=CC=CC=1>[C:1]1([C:7]2[N:8]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][P:32]([O:36][CH2:37][CH3:38])(=[O:39])[O:33][CH2:34][CH3:35])[C:9]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 31215Triethyl phosphiteHCID 229163771-(7-Bromoheptyl)-2,4,5-triphenylimidazole

Product 1

HCID 22916421Diethyl 7-(2,4,5-triphenylimidazol-1-yl)heptane-phosphonateYield 35%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 2,4,5-triphenyl-1-(7-bromoheptyl)-imidazole (0.95 g) and triethyl phosphite (1.66 g) in xylene (5 ml) was heated at reflux temperature for 20 hours. The mixture was evaporated to an oil and chromatographed on silica gel (ethyl acetate/ethanol) to give diethyl 7-(2,4,5-triphenylimidazol-1-yl)heptane-phosphonate (0.37 g, 35%) as a light brown oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 20 hours
  3. customThe mixture was evaporated to an oil
  4. customchromatographed on silica gel (ethyl acetate/ethanol)

Sources & evidence

ORD record
ord-b872718e0dee4eae9146f06ae2e83750
Source dataset
uspto-grants-1997_07
Patent number
US05648373

Reaction notes

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