Reaktion #738554

ord-e9a8134d776e4f1bad2d4e2d1dc734d8

Reaktionsgleichung

C[C@]12CC[C@@H]3c4ccc(O)cc4CC[C@H]3[C@@H]1CCC2=O
estrone
C1=COCCC1
DHP
→
C[C@]12CC[C@@H]3c4ccc(OC5CCCCO5)cc4CC[C@H]3[C@@H]1CCC2=O
ether
C[C@]12CC[C@@H]3c4ccc(OC5CCCCO5)cc4CC[C@H]3[C@@H]1CCC2=O
3-Tetrahydropyranyloxyestra-1,3,5 (10)-trien-17-one

Edukte

—
compound 35
C[C@]12CC[C@@H]3c4ccc(O)cc4CC[C@H]3[C@@H]1CCC2=O
estrone
C1=COCCC1
DHP

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

The THP ether 60, which was prepared from estrone 1 (6.3 g, 23.3 mmol) and DHP (3.0 g, 33 mmol) using the same procedure as described for compound 35, was obtained as a white solid (7.5 g, 91%): 1H NMR (300 MHz, CDCl3) δ0.91 (s, 3, CH3), 2.89 (m, 2), 3.60 (m. 1), 3.92 (m, 1), 5.40 (m, 1), 6.81 (d, J=2.5 Hz, 1, ArH), 6.86 (dd, J=2.5, 8.5 Hz, 1, ArH), 7.20 (d, J=8.5 Hz, 1, ArH).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06281205B1uspto-grants-2001_08