Réaction #2347539

Équation de réaction

1,2,3,4-tetrahydro-6-methoxy-1,4-methanonaphthalene-5,8-diol

EtOAc

→

53

1,2,3,4-Tetrahydro-6-methoxy-1,4-methanonaphthalene-5,8-dione

Solvants

water

CHCl3

CHCl3

Conditions de réaction

Traitement

1. 1
   AutreThe vigorously stirred reaction immediately became orange
2. 2
   Autrethe total consumption of the
3. 3
   AutreThe layers were separated
4. 4
   Extractionthe aqueous portion extracted with CHCl3 (2×20 mL)
5. 5
   LavageThe combined organic portion was washed with half saturated brine (30 mL)
6. 6
   Filtrationfiltered through cotton
7. 7
   Autrethe solvent removed in vacuo
8. 8
   FiltrationThe residue was filtered through a plug of silica gel with CHCl3 elution
9. 9
   AutreSolvent removal

Mode opératoire

To a vigorously stirred solution of NaIO4 (1.69 g, 7.89 mmol, Baker) in water (50 mL), there was added a solution of 1,2,3,4-tetrahydro-6-methoxy-1,4-methanonaphthalene-5,8-diol (52, 543 mg, 2.63 mmol) in CHCl3 (20 mL). The vigorously stirred reaction immediately became orange. The reaction was allowed to stir for 15 min at rt at which point TLC analysis (10% EtOAc, 90% CHCl3) showed the total consumption of the organic starting material and the formation of a yellow, higher Rf spot. The layers were separated and the aqueous portion extracted with CHCl3 (2×20 mL). The combined organic portion was washed with half saturated brine (30 mL), filtered through cotton and the solvent removed in vacuo. The residue was filtered through a plug of silica gel with CHCl3 elution. Solvent removal gave 53 as a yellow semisolid. Scraping this semisolid with a spatula resulted in a yellow powder. This was further dried in vacuo (470 mg, 88%, pure by TLC and 1H NMR); mp 106°-108° C.; 1H NMR (CDCl3) δ1.16 (m, 2H), 1.40 (d, J=9.0 Hz, 1H), 1.63 (d, J=8.7 Hz, 1H), 1.91 (m, 2H), 3.50 (m, 2H), 3.78 (s, 3H), 5.72 (s, 1H).

Source