Trimethyl phosphite → HCID 54194150, Verbindung

HRID 233439

Reaktionsgleichung

Reaktionsgleichung von HRID 233439
Cl[CH2:2][C:3]1[C:4]2[C:9]([CH:10]=[C:11]3[C:16]=1[CH:15]=[CH:14][CH:13]=[CH:12]3)=[CH:8][CH:7]=[CH:6][CH:5]=2.[CH3:17][O:18][P:19]([O:22]C)[O:20][CH3:21]>>[CH3:17][O:18][P:19]([CH2:2][C:3]1[C:4]2[C:9]([CH:10]=[C:11]3[C:16]=1[CH:15]=[CH:14][CH:13]=[CH:12]3)=[CH:8][CH:7]=[CH:6][CH:5]=2)(=[O:22])[O:20][CH3:21]

Komponenten

3

Edukt 2

HCID 8472Trimethyl phosphiteHCID 323859-(Chloromethyl)anthracene

Produkt 1

HCID 54194150HCID 54194150, VerbindungAusbeute 40,5 %

Versuchsvorschrift

A solution of 9-(chloromethyl)anthracene (2.5 g, 0.011M) in trimethylphosphite (5 mL, 5.26 g, 0.042 M) is heated at reflux temperature for 72 hours. Excess trimethylphosphite is removed under reduced pressure and the residue is chromatographed over silica gel (400 g, 40-63 μm, CH2Cl2, 50 mL fractions) using CH2Cl2 (60 fractions) and 2% CH3OH in CH2Cl2 for the remaining fractions. Fractions 86-93 (2.99 g) are found to contain desired material and an impurity and are rechromatographed (400 g silica gel, 40-63 lam, CH2Cl2, 50 mL fractions) using 2.5% acetone-CH2Cl2 to elute the column. Fractions 100-160 contains compound (1.495 g, 0.00498M, 45%) as a yellow solid. Crystallization from ethyl acetate gives the title compound (1.34 g) as yellow needles, mp 152°-153° C.

Aufarbeitung

  1. temperatureat reflux temperature for 72 hours
  2. customExcess trimethylphosphite is removed under reduced pressure
  3. customthe residue is chromatographed over silica gel (400 g, 40-63 μm, CH2Cl2, 50 mL fractions)
  4. customan impurity and are rechromatographed (400 g silica gel, 40-63 lam, CH2Cl2, 50 mL fractions)
  5. washto elute the column
  6. customCrystallization from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-e8fd225220224ebe9614ca6f948f60e1
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05593980

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