Reaktion #42216

Reaktionsgleichung

(±)-2-hydroxy-3-(5-hydroxy-8-methoxy-1,2,3,4-tetrahydro-1,4-ethanonaphthalen-6-yl)propyl 4-methylbenzenesulfonate

triphenylphosphine

diethylazodicarboxylate

→

(±)-(5-methoxy-2,3,6,7,8,9-hexahydro-6,9-ethanonaphtho[1,2-b]furan-2-yl)methyl 4-methylbenzenesulfonate

Ausbeute 75.1%

Reaktionsbedingungen

Vorschrift

Treatment of (±)-2-hydroxy-3-(5-hydroxy-8-methoxy-1,2,3,4-tetrahydro-1,4-ethanonaphthalen-6-yl)propyl 4-methylbenzenesulfonate (15.14 g, 35.0 mmol) with triphenylphosphine (10.10 g, 38.5 mmol) followed by diethylazodicarboxylate (6.71 g, 38.5 mmol) generally according to the procedure described for Intermediate 5 afforded 10.9 g (75%) of (±)-(5-methoxy-2,3,6,7,8,9-hexahydro-6,9-ethanonaphtho[1,2-b]furan-2-yl)methyl 4-methylbenzenesulfonate as a white solid. mp 136-141° C.; Anal. calcd. for C23H26O5S: C, 66.64; H, 6.32. Found: C, 66.53; H, 6.51.

Quelle