Reaktion #483778

Reaktionsgleichung

Tert-butyl hydroperoxide

hydroxymethyldihydro-pyran

ethyl acetate

→

oil

Ausbeute 70.0%

(3,7-Dioxa-bicyclo[4.1.0]hept-1-yl)-methanol

Ausbeute 70.0%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe reaction
2. 2
   Waschenwashed with 1 M hydrochloric acid
3. 3
   Waschena wash with a saturated sodium bicarbonate solution
4. 4
   TrocknenThe ethyl acetate layer was dried over sodium sulfate
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated in vacuo

Vorschrift

Tert-butyl hydroperoxide (5.5M, 4.73 mmoles) was added to a mixture of vanadyl acetoacetonate (0.058 g, 0.22 mmoles) and hydroxymethyldihydro-pyran (0.5 g, 4.38 mmoles) in 16.2 ml of toluene at 85° C. After stirring for 5 minutes, TLC showed the reaction to be complete. The mixture was diluted with ethyl acetate and washed with 1 M hydrochloric acid followed by a wash with a saturated sodium bicarbonate solution. The ethyl acetate layer was dried over sodium sulfate, filtered and concentrated in vacuo to yield a light yellow oil (0.4 g, 70%). 1H NMR (D6 acetone, 400 MHz) δ 3.21 (bs, 1H), 3.36-3.42 (m, 2H), 3.48 (dd, J=6.64 Hz and 12.04 Hz, 1H), 3.6 (dd, J=5.61 Hz and 12.04 Hz, 1H), 3.74 (d, J=13.07 Hz, 1H), 3.87 (dd, J=5.6 Hz and 6.64 Hz, 1H), 4.02 (d, J=13.07 Hz, 1H).

Quelle