4-Bromobutyric acid → 4-Bromobutanoic Acid 9-Fluorenylmethyl Ester

HRID 329544

Reaktionsgleichung

Reaktionsgleichung von HRID 329544
[Br:1][CH2:2][CH2:3][CH2:4][C:5]([OH:7])=[O:6].[CH:8]1[C:20]2[CH:19]([CH2:21]O)[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]=2[CH:11]=[CH:10][CH:9]=1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH:8]1[C:20]2[CH:19]([CH2:21][O:6][C:5](=[O:7])[CH2:4][CH2:3][CH2:2][Br:1])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]=2[CH:11]=[CH:10][CH:9]=1

Komponenten

5

Edukt 2

HCID 758094-Bromobutyric acidHCID 904669H-Fluorene-9-methanol

Produkt 1

HCID 145062184-Bromobutanoic Acid 9-Fluorenylmethyl EsterAusbeute 86,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

DDC (6.00 g, 29 mmol) was added in one portion to a cooled solution (0° C.) of 4-bromobutyric acid (5.00 g, 29.9 mmol), 4-(dimethylamino)pyridine (353 mg, 2.9 mmol) and 9-fluorenemethanol (5.63 g, 25 mmol) in CH2Cl2 (150 mL). The mixture was allowed to stand at 4° C. for 18 h, and then filtered. The filtrate was evaporated to dryness under reduced pressure. The residue was dissolved in EtOAc and the solution washed sequentially with 1N NaHCO3, 1N HCl and H2O. The solution was dried (Na2 -SO4) and evaporated to dryness under reduced pressure. The residue was purified by flash chromatography on silica gel (200 g) using hexane-EtOAc (15:1) as the eluant to give the pure title compound as an oil (7.5 g).

Aufarbeitung

  1. filtrationfiltered
  2. customThe filtrate was evaporated to dryness under reduced pressure
  3. dissolutionThe residue was dissolved in EtOAc
  4. washthe solution washed sequentially with 1N NaHCO3, 1N HCl and H2O
  5. customThe solution was dried (Na2 -SO4)
  6. customevaporated to dryness under reduced pressure
  7. customThe residue was purified by flash chromatography on silica gel (200 g)

Quellen und Nachweise

ORD-Eintrag
ord-e881caaf12d945be80405e4641a3e0c4
Quelldatensatz
uspto-grants-1990_01
Patentnummer
US04891358

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