Succinic anhydride → Succinic acid Fluorenylmethyl Ester

HRID 440452

Reaktionsgleichung

Reaktionsgleichung von HRID 440452
[C:1]1([CH2:14][OH:15])[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.CN(C1C=CC=CN=1)C.[C:25]1(=[O:31])[O:30][C:28](=[O:29])[CH2:27][CH2:26]1>N1C=CC=CC=1>[C:1]1([CH2:14][O:15][C:25](=[O:31])[CH2:26][CH2:27][C:28]([OH:30])=[O:29])[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Komponenten

5

Edukt 3

HCID 7922Succinic anhydrideHCID 218852-DimethylaminopyridineHCID 523071-Fluorenemethanol

Produkt 1

HCID 69916676Succinic acid Fluorenylmethyl EsterAusbeute 64,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

Fluorenylmethanol (0.90 g, 4.5 mmol) and dimethylaminopyridine (50 mg) were dissolved in 10 ml dry pyridine. Succinic anhydride (0.50 g, 5.0 mmol) was added and the solution stirred overnight. The solvent was removed under reduced pressure, sodium bicarbonate added (50 ml), the solution extracted with ethyl acetate (50 ml), and the organic layer discarded. The aqueous layer was acidified to pH 2, extracted with ethyl acetate (2×100 ml), washed with brine, and the solvent removed under reduced pressure. The residue was purified by flash chromatography (ethyl acetate/hexane 2:1 as eluant) to give 0.86 g product (2.9 mmol, 64%). 1H NMR: (CDCl3, 200 MHz) δ7.8-7.26 (8H, m, ArH), 4.43 (2H, d, J=6.5 Hz, CHCH2OCO), 4.23 (1H, t, J=6.5 Hz, CHCH2OCO), 2.70 (4H, s, OCOCH2CH2COO).

Aufarbeitung

  1. customThe solvent was removed under reduced pressure, sodium bicarbonate
  2. additionadded (50 ml)
  3. extractionthe solution extracted with ethyl acetate (50 ml)
  4. extractionextracted with ethyl acetate (2×100 ml)
  5. washwashed with brine
  6. customthe solvent removed under reduced pressure
  7. customThe residue was purified by flash chromatography (ethyl acetate/hexane 2:1 as eluant)

Quellen und Nachweise

ORD-Eintrag
ord-99abc67d5cec4c7e907ea4893a023835
Quelldatensatz
uspto-grants-1996_05
Patentnummer
US05519134

Verknüpfte Notizen

Wird geladen…