Acetone → 1-Acetoxy-3-methoxyestra-1,3,5(10)-trien-17-one
Reaction equation
[C:1]([O:4][C:5]1[C:22]2[C@@H:21]3[C@H:12]([C@H:13]4[C@@:17]([CH2:19][CH2:20]3)([CH3:18])[C:16](=[O:23])[CH2:15][CH2:14]4)[CH2:11][CH2:10][C:9]=2[CH:8]=[C:7]([OH:24])[CH:6]=1)(=[O:3])[CH3:2].[CH3:25]C(C)=O>>[C:1]([O:4][C:5]1[C:22]2[C@@H:21]3[C@H:12]([C@H:13]4[C@@:17]([CH2:19][CH2:20]3)([CH3:18])[C:16](=[O:23])[CH2:15][CH2:14]4)[CH2:11][CH2:10][C:9]=2[CH:8]=[C:7]([O:24][CH3:25])[CH:6]=1)(=[O:3])[CH3:2]Participants
3
Procedure
1-Acetoxy-3-hydroxyestra-1,3,5(10)-trien-17-one (7.6 g, 23 mM) is added to 600 ml of anhydrous acetone in a 3-neck, 1 liter round bottom flask equipped with condenser, magnetic stirring bar, drying tube and pressure-compensated addition funnel. Dimethyl sulfate (3.2 g, 25 mM) is added and the resulting suspension is refluxed for 16 hrs, and then filtered while still warm. The filter cake is washed repeatedly with anhydrous acetone, and the combined filtrates are evaporated in vacuo. The residue is recrystallized from acetone-water to obtain 1-acetoxy-3-methoxyestra-1,3,5(10)-trien-17-one, yield 6.2 g (80%), m.p. 144°-145°. Further recrystallization from CH2Cl2 -hexane gives material of m.p. 150°-151°.
Workup
- customequipped with condenser, magnetic stirring bar
- customdrying tube and pressure-compensated addition funnel
- additionDimethyl sulfate (3.2 g, 25 mM) is added
- temperaturethe resulting suspension is refluxed for 16 hrs
- filtrationfiltered
- temperaturewhile still warm
- washThe filter cake is washed repeatedly with anhydrous acetone
- customthe combined filtrates are evaporated in vacuo
- customThe residue is recrystallized from acetone-water
Sources & evidence
- ORD record
- ord-4fa104b4f9f845d68230a826d14986e6
- Source dataset
- uspto-grants-1978_06
- Patent number
- US04096253
Reaction notes
Loading…