Triethyl phosphite → Diethyl 7-(1,4,5-triphenylimidazol-2-yl-oxy)heptanephosphonate

HRID 1376374Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1376374
C1([N:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:10]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:9](CCCCCCCBr)[C:8]2=[O:32])C=CC=CC=1.[P:33]([O:40][CH2:41][CH3:42])([O:37]CC)[O:34][CH2:35][CH3:36]>C1(C)C(C)=CC=CC=1>[C:12]1([N:9]2[C:10]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[C:11]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:7]=[C:8]2[O:32][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:10][CH2:11][P:33]([O:34][CH2:35][CH3:36])(=[O:37])[O:40][CH2:41][CH3:42])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

4

Edukt 2

HCID 31215Triethyl phosphiteHCID 229163881,4,5-Triphenyl-3-(7-bromoheptyl)imidazol-2-one

Produkt 1

HCID 10098964Diethyl 7-(1,4,5-triphenylimidazol-2-yl-oxy)heptanephosphonate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7237O-XyleneLösungsmittel

Versuchsvorschrift

A mixture of 1,4,5-triphenyl-3-(7-bromoheptyl)-imidazol-2-one (1.0 g) and triethyl phosphite (1.66 g) was heated at reflux temperature in xylene (5 ml) for 40 hours. The solution was evaporated to an oil and re-evaporated from ethanol. The oil was partitioned between ether and water, the ether solution was separated, dried over magnesium sulphate and evaporated to an oil which was chromatographed on silica gel (ethyl acetate) to give diethyl 7-(1,4,5-triphenylimidazol-2-yl-oxy)heptanephosphonate as an oil which solidified on standing to a white solid (0.83 g; 75%), m.p. 76°-7° C. Found: C, 70.49; H, 7.40; N, 4.94%; C32H39N204P; Requires: C, 70.31; H, 7.19; N, 5.12%.

Aufarbeitung

  1. temperaturewas heated
  2. customThe solution was evaporated to an oil
  3. customre-evaporated from ethanol
  4. customThe oil was partitioned between ether and water
  5. customthe ether solution was separated
  6. dry with materialdried over magnesium sulphate
  7. customevaporated to an oil which
  8. customwas chromatographed on silica gel (ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-24d54e9fbf84484b8995f6ab67c0455f
Quelldatensatz
uspto-grants-1997_09
Patentnummer
US05663053

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