Dimethylformamide → 3-Cyclopentyloxy-6-fluoro-4-methoxybenzaldehyde

HRID 993273

Reaktionsgleichung

Reaktionsgleichung von HRID 993273
[F:1][C:2]1[C:7]([CH:8]=[O:9])=[CH:6][C:5]([OH:10])=[C:4]([O:11][CH3:12])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.[CH:24]1(Br)[CH2:28][CH2:27][CH2:26][CH2:25]1>O>[CH:24]1([O:10][C:5]2[CH:6]=[C:7]([C:2]([F:1])=[CH:3][C:4]=2[O:11][CH3:12])[CH:8]=[O:9])[CH2:28][CH2:27][CH2:26][CH2:25]1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 5981462-Fluoro-5-hydroxy-4-methoxybenzaldehyde

Produkt 1

HCID 221457953-Cyclopentyloxy-6-fluoro-4-methoxybenzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 6-fluoro-3-hydroxy-4-methoxybenzaldehyde (2 g), potassium carbonate (1.66 g) and anhydrous dimethylformamide (20 mL) is treated with cyclopentyl bromide (1.62 mL) and heated on a steam bath for 43 hours. The mixture is cooled, poured into water (200 mL) and extracted with diethyl ether (3×100 mL). The combined ethereal extracts are washed with sodium hydroxide solution (2×50 mL; 2 N), and brine (2×50 mL), dried over magnesium sulphate and concentrated. The residual brown oil is subjected to flash chromatography [a solvent gradient of 9:1 to 4:1 v/v petroleum ether (b.p. 60-80° C.) and ethyl acetate is used as eluent on a silica gel column] to give 3-cyclopentyloxy-6-fluoro-4-methoxybenzaldehyde (1.42 g) in the form of a yellow oil. [NMR (CDCl3): 10.22 (s, 1H), 7.27 (d, 1H, J=8 Hz), 6.63 (d, 1H, J=16 Hz), 4.81-4.76 (m, 1H), 3.91 (s, 3H), 2.01-1.57 (m, 8H)].

Aufarbeitung

  1. temperatureheated on a steam bath for 43 hours
  2. temperatureThe mixture is cooled
  3. extractionextracted with diethyl ether (3×100 mL)
  4. washThe combined ethereal extracts are washed with sodium hydroxide solution (2×50 mL; 2 N), and brine (2×50 mL)
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-ba5d052ba3cc4e42bcde29805dd04727
Quelldatensatz
uspto-grants-2002_10
Patentnummer
US06472412B1

Verknüpfte Notizen

Wird geladen…