KlementineJBS
commented
3 years ago 11.05.21
- quenched with NaHCO3 (20 mL, sat.)
- 20 mL DCM + 20 mL brine
- rotvapped off DCM and MeOH
- 40 mL brine + 20 mL isopropanol
- extraction 1
- 20 mL DCM + brine 20 mL
- rovapped off DCM
Actual extraction process
- 100 mL ether, 2 x 75 mL ether
- NB: lots of fluffy brown emulsion - need to swirl sep funnel to get it to settle at bottom
- brine wash (150 mL)
- dried over MgSO4
- rotvapped down to give dark red liquid
Synthesis of ferrocenyl methyl ester
Link to HIRAC.
Outcome
27 mg (0.111 mmol), 13%
MW product = 244.02
Reaction Scheme
Method
Methanol (5 mL) was cooled to 0 C and acetyl chloride (0.2 mL, 2.80 mmol) was added dropwise. The mixture was stirred for 15 minutes before ferrocenecarboxylic acid (203 mg, 0.882 mmol) was added. The mixture was then warmed to room temperature and refluxed for 3 hours. NaHCO3 (20 mL) was used to quench the reaction and excess methanol was removed by rotary evaporation. The mixture was then extracted using diethyl ether (3 x 80 mL), washed with brine (150 mL) and dried over MgSO4 before being concentrated under reduced pressure.
To consider