Triphenyl phosphite → 4-[2-[4-(t-Butyl)phenyl]ethoxy]pteridine

HRID 2226838

Reaktionsgleichung

Reaktionsgleichung von HRID 2226838
[OH:1][C:2]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][N:10]=2)[N:5]=[CH:4][N:3]=1.P(OC1C=CC=CC=1)(OC1C=CC=CC=1)OC1C=CC=CC=1.ClCl.[C:36]([C:40]1[CH:45]=[CH:44][C:43]([CH2:46][CH2:47]O)=[CH:42][CH:41]=1)([CH3:39])([CH3:38])[CH3:37]>C(Cl)Cl.C1(C)C=CC=CC=1.N1C=CC=CC=1>[C:36]([C:40]1[CH:41]=[CH:42][C:43]([CH2:46][CH2:47][O:1][C:2]2[C:11]3[C:6](=[N:7][CH:8]=[CH:9][N:10]=3)[N:5]=[CH:4][N:3]=2)=[CH:44][CH:45]=1)([CH3:39])([CH3:38])[CH3:37]

Komponenten

8

Edukt 4

HCID 7540Triphenyl phosphiteHCID 24526ChlorineHCID 79410p-tert-Butylphenethyl alcoholHCID 178518044HCID 178518044, Verbindung

Produkt 1

HCID 149961134-[2-[4-(t-Butyl)phenyl]ethoxy]pteridine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 1049PyridineLösungsmittelHCID 1140TolueneLösungsmittelHCID 6344DichloromethaneLösungsmittel3×

Reaktionsbedingungen

Temperatur
10 °C

Versuchsvorschrift

To a suspension of 2 g of 4-hydroxypteridine in 20 mL of CH2Cl2 under nitrogen was added 1.2 g of pyridine. The mixture was cooled to -30° C. and over a 15 minute period a solution of 4.82 g of triphenyl phosphite in CH2Cl2 was added simultaneously with addition of chlorine gas. The mixture was stirred for one and one half hours while maintaining the temperature at -15° to -20° C. The mixture was then allowed to warm to 10° C., and a solution of 2.67 g of 2-[4-(t-butyl)phenyl]ethanol in CH2Cl2 was added. The resulting mixture was refluxed for 45 minutes, then cooled and diluted into toluene. The toluene solution was washed with dilute base, then filtered through phase separating paper and concentrated in vacuo. The resulting bluish oil was adsorbed onto silica gel and chromatographed (silica gel, CH2Cl2 →80% CH2Cl2, 20% EtOAc). Fractions containing the major product were combined. The product was then recrystallized from petroleum ether/CH2Cl2. Yield 60 mg. M.P. 149° C.

Aufarbeitung

  1. temperaturewhile maintaining the temperature at -15° to -20° C
  2. temperatureThe resulting mixture was refluxed for 45 minutes
  3. temperaturecooled
  4. washThe toluene solution was washed
  5. additionwith dilute base
  6. filtrationfiltered through phase
  7. customseparating paper
  8. concentrationconcentrated in vacuo
  9. customchromatographed (silica gel, CH2Cl2 →80% CH2Cl2, 20% EtOAc)
  10. additionFractions containing the major product
  11. customThe product was then recrystallized from petroleum ether/CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-99d8239b548343e0849d911e6be2e38d
Quelldatensatz
uspto-grants-1994_09
Patentnummer
US05350749

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