Reaction #1747894

Reaction equation

oestrone

potassium carbonate

benzyl bromide

→

3-benzyloxyestra-1,3,5(10)-trien-17-one

Yield 78.0%

Solvents

DMF

Conditions

Workup

1. 1
   Otherquenched with H2O
2. 2
   Extractionextracted with EtOAc
3. 3
   WashThe combined organic layers were washed with H2O, saturated aqueous NaCl
4. 4
   Dryingdried (MgSO4)
5. 5
   FiltrationThe desiccant was filtered
6. 6
   Otherthe solvent was evaporated at reduced pressure
7. 7
   OtherThe residue was triturated with Et2O
8. 8
   Filtrationfiltered
9. 9
   Otherevaporated

Procedure

To a solution of oestrone (3.35 g, 12.39 mmol) in DMF (50 ml) were added potassium carbonate (3.45 g, 25 mmol) and benzyl bromide (2.25 ml, 18.75 mmol) at room temperature under an atmosphere of nitrogen. The reaction mixture was stirred for 24 h, then quenched with H2O, and extracted with EtOAc. The combined organic layers were washed with H2O, saturated aqueous NaCl, and then dried (MgSO4). The desiccant was filtered and the solvent was evaporated at reduced pressure. The residue was triturated with Et2O, filtered and evaporated to afford 3.48 g (78% yield) of 3-benzyloxyestra-1,3,5(10)-trien-17-one BLE99049 as a white solid.

Source