Reaktion #41879

Reaktionsgleichung

water

(1-Phenyl-cyclopentyl)-methanol

Dess-Martin Periodine

sodium bicarbonate

→

1-Phenyl-cyclopentanecarbaldehyde

Ausbeute 81.8%

Lösungsmittel

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAfter completion of the reaction
2. 2
   Extraktionextracted with DCM (50 mL)
3. 3
   TrocknenThe organic mixture was then dried over sodium sulfate
4. 4
   Einengenconcentrated under reduced pressure

Vorschrift

To a solution of (1-Phenyl-cyclopentyl)-methanol (1.0 g, 5.7 mmol) in DCM (20 mL) was added Dess-Martin Periodine (6.8 mmol, 1.2 eq) and sodium bicarbonate (6.8 mmol, 1.2 eq) at 0° C. The reaction mixture stirred at this temperature for 2 h and allowed to warm up slowly to room temperature. After completion of the reaction, the mixture was poured into water (50 mL) and extracted with DCM (50 mL). The organic mixture was then dried over sodium sulfate and concentrated under reduced pressure to give 1-Phenyl-cyclopentanecarbaldehyde (812 mg) which was immediately used to synthesize title compound (14 mg) from Intermediate B (20 mg, 0.025 mmol) following general procedures D and B. LC-MS (m/z): 923.

Quelle