Water → (1R,4R)-1,4-bis(4-nitrophenyl)butane-1,4-diol

HRID 1470912

Reaktionsgleichung

Reaktionsgleichung von HRID 1470912
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:24])[CH2:11][CH2:12][C:13]([C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)=[O:14])=[CH:6][CH:5]=1)([O-:3])=[O:2].[BH4-].[Na+].O>C1COCC1>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([OH:24])[CH2:11][CH2:12][CH:13]([C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)[OH:14])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Komponenten

5

Edukt 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 137628911,4-Bis(4-nitrophenyl)butane-1,4-dione

Produkt 1

HCID 59616924(1R,4R)-1,4-bis(4-nitrophenyl)butane-1,4-diolAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of the product from Example 1A (1.0 g, 3.05 mmol) in anhydrous THF (30 ml) at 0° C. was added sodium borohydride (0.357 g, 9.44 mmol). The resulting mixture was stirred at 50° C. overnight. The cooled mixture was poured into water, extracted with ethyl acetate, dried over Na2SO4, filtered and concentrated in vacuo. The resulting solid was triturated with dichloromethane to give a tan solid that was collected by filtration and dried to give the title compound (0.82 gm, 81% yield).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe resulting solid was triturated with dichloromethane
  6. customto give a tan solid
  7. filtrationthat was collected by filtration
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-22d0ca60dfa64adcaf11d57a2cf794e2
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09006387B2

Verknüpfte Notizen

Wird geladen…