Reaktion #160812

Reaktionsgleichung

3-methylidene-4-(pent-4-en-1-yl)tetrahydro-2H-pyran

→

title compound

3,4,4a,5,6,7-hexahydro-1H-isochromene

Lösungsmittel

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction was degassed three times
2. 2
   workup.ADDITIONZhan-1b (58.3 mg, 0.079 mmol) was added at 0° C
3. 3
   SonstigeThe reaction mixture was degassed again
4. 4
   EinengenThe mixture was concentrated under reduced pressure (280 mmhg)
5. 5
   SonstigeThe residue was purified by column chromatography on silica gel

Vorschrift

3-methylidene-4-(pent-4-en-1-yl)tetrahydro-2H-pyran (1320 mg, 7.94 mmol) was added to CH2Cl2 (159.00 ml) at RT. The reaction was degassed three times. Zhan-1b (58.3 mg, 0.079 mmol) was added at 0° C. The reaction mixture was degassed again and then stirred at room temperature for 1 h. The mixture was concentrated under reduced pressure (280 mmhg). The residue was purified by column chromatography on silica gel to provide the title compound. 1H NMR (500 MHz, CDCl3) δ 5.54 (d, 1H, J=2.2 Hz), 4.06 (d, 1H, J=122 Hz), 3.97 (dd, 1H, J=4.4 Hz, 11.2 Hz), 3.84-3.91 (m, 1H), 3.46-3.53 (m, 1H), 2.21 (bs, 1H), 1.92-2.19 (m, 2H), 1.80-1.89 (m, 1H), 1.68-1.86 (m, 2H), 1.36-1.48 (m, 2H), 1.16-1.26 (m, 1H).

Quelle