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KlementineJBS / USYD_PhD_ELN

This repository forms the electronic laboratory notebook (ELN)for Klementine Burrell-Sander's PhD's
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KBS14-8 - Methyl esterification of ferrocenecarboxylic acid #13

Closed KlementineJBS closed 2 years ago

KlementineJBS commented 2 years ago

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

KBS14 ALTERNATIVE (DBU method) .docx

Reaction Scheme

Ferrocenecarboxylic acid to ferrocene methyl ester

Outcome

155.4 mg (0.637 mmol), 70% (still slightly wet)

KlementineJBS commented 2 years ago

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 commented 2 years ago

17.06.22

  1. TLC'd at 10 am
  1. Cooled to room temperature and diluted with water (10 mL), brine (30 mL)
  2. Extracted with EtOAc (40 mL)
  3. Added extra water (40 mL)
  4. Extracted with EtOAc (50 mL, then 40 mL)
  5. Washed with HCl (2 x 100 mL, 1 M)
  6. Washed with NaHCO3 (2 x 100 mL, sat.)
  7. Washed with brine (100 mL)
  8. Dried over MgSO4
  9. Rotovapped down

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

KlementineJBS commented 2 years ago

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.

KBS14-8 cr

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

KlementineJBS commented 2 years ago

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