Reaktion #2073798

Reaktionsgleichung

3′,4′-dihydro-1′H-spiro[[1,3]dioxolane-2,2′-naphthalene]-6′-carbonitrile

TFA CH2Cl2

H2O

→

6-cyano-2-tetralone

Ausbeute 122.1%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITleft
2. 2
   Sonstigea new spot (Rf˜0.90) formed
3. 3
   Einengenconcentrated in vacuo
4. 4
   workup.ADDITIONThe residue was diluted with toluene (50 mL)
5. 5
   Einengenconcentrated again

Vorschrift

A mixture of 3′,4′-dihydro-1′H-spiro[[1,3]dioxolane-2,2′-naphthalene]-6′-carbonitrile (230 mg, 1.1 mmol), 20% TFA/CH2Cl2 (4 mL), and H2O (˜0.1 mL) was stirred at room temperature for 16 hours. TLC (50% EtOAc/hexanes) showed no starting material (Rf˜0.95) left and a new spot (Rf˜0.90) formed. The mixture was diluted with toluene (50 mL) and then concentrated in vacuo. The residue was diluted with toluene (50 mL) and concentrated again to give 0.23 g (100%) of 6-cyano-2-tetralone as an orange solid. 1H NMR (300 MHz, CDCl3): δ 7.55 (s, 1H), 7.53 (d, 1H, J=7.8 Hz), 7.24 (d, 1H, J=7.8 Hz), 3.64 (s, 2H), 3.11 (t, 2H, J=6.6 Hz), 2.58 (t, 2H, J=6.6 Hz). As shown by the 1H NMR, the product was >95% pure, thus it was used without further purification.

Quelle