Reaktion #76334

Reaktionsgleichung

aldehyde

3-(dihydro-2-furanyl)benzaldehyde

2,6-lutidine

hydrogen

→

3-(tetrahydro-2-furanyl)phenylmethanol

Ausbeute 70.0%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe slurry was filtered through celite
2. 2
   Sonstigethe solvent was removed
3. 3
   Waschenwashed with 1 N HCl and brine
4. 4
   TrocknenThe organic layer was dried (MgSO4)
5. 5
   Sonstigeevaporated

Vorschrift

Ex-608C) A THF (15 mL) solution of the aldehyde from EX-608B (0.70 g, 4.0 mmol) and 2,6-lutidine (0.46 mL, 4.0 mmol) was stirred in a hydrogen atmosphere (50 psi) in the presence of 10% Pd/C (0.29 g) for 18 h at room temperature. The slurry was filtered through celite, and the solvent was removed. The residue was taken up in ethyl acetate and washed with 1 N HCl and brine. The organic layer was dried (MgSO4) and evaporated to give 0.50 g (70%) of the desired 3-(tetrahydro-2-furanyl)phenylmethanol product as a yellow oil. The formation of the desired product was monitored by the disappearance of the aldehyde (δ˜10) and olefin peaks in the 1H NMR spectrum.

Quelle