KBS14-8 - Methyl esterification of ferrocenecarboxylic acid about usyd_phd_eln

[KlementineJBS]

16.06.22

1. Dissolved 208 mg (0.904 mmol) ferrocenecarboxylic acid in DMC (4 mL)
2. Added DBU (0.155 mL, 1.04 mmol, 1.2 equiv.)
3. Heated to reflux (90 C) from 11.15 am
4. Added more DBU (0.055 mL, 0.347 mmol, 0.4 equiv.) at 4.30 pm after TLCing

[KlementineJBS]

17.06.22

5. TLC'd at 10 am

6. Cooled to room temperature and diluted with water (10 mL), brine (30 mL)
7. Extracted with EtOAc (40 mL)
8. Added extra water (40 mL)
9. Extracted with EtOAc (50 mL, then 40 mL)
10. Washed with HCl (2 x 100 mL, 1 M)
11. Washed with NaHCO3 (2 x 100 mL, sat.)
12. Washed with brine (100 mL)
13. Dried over MgSO4
14. Rotovapped down

Vial (empty) = 15.8218
Vial (product) = 15.9772
Product = 155.4 mg

[KlementineJBS]

20.06.22

H NMR

KBS14-8 cr_1.zip

KBS14-8 cr processed.pdf

1H NMR (300 MHz, CDCl3) δ 4.80, 4.40, 4.21, 3.81.

Appears to be very clean except for some residual water (1.55). Will likely carry through without further characterisation.

[KlementineJBS]

20220701_KBS14-8.d.zip
KBS14-8.pdf