KBS14-7 - Methyl esterification of ferrocenecarboxylic acid

[KlementineJBS]

Link to HIRAC and master page. Method adapted from Shieh et al., 2002.

KBS14 ALTERNATIVE (DBU method) .docx

Reaction Scheme

Outcome

Mass of 123.3 mg (unpurified, containing more SM than product). May be due to not allowing reaction to go to completion - next time, will add 1.2 equiv. of DBU at beginning and possibly allow longer reaction times.

[KlementineJBS]

14.06.22

1. Dissolved 200 mg (0.868 mmol) ferrocenecarboxylic acid in DMC (4 mL).
2. Added 132 mg DBU (0.129 mL, 0.868 mmol, 1 equiv.)
3. Heated to reflux (90 C) at 10.10 am.
4. After TLCing at 1.45 pm and 4.30 pm, more DBU (0.129 mL, 0.868 mmol) was added

[KlementineJBS]

15.06.22

5. TLC'd again at 9.45 am. Determined reaction was partially complete, and began work up

6. Cooled to room temperature and diluted with water (15 mL) and brine (20 mL)
7. Extracted with ethyl acetate (3 x 40 mL)
8. Washed with 1 M HCl (2 x 75 mL)
9. Washed with NaHCO3 (2 x 75 mL)
10. Washed with brine (75 mL)
11. Dried over MgSO4
12. Rotovapped down

Vial (empty) = 15.9418 g Vial (product) = 16.0651 g Mass = 123.3 mg

NMR

Unfortunately, H NMR indicates very little product is present (small peaks are product, large peaks are SM). Product is estimated to be ~ 1/6 of total mass, i.e. ~ 20 mg, so further purification was not pursued.