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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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KBS15-5 - Reduction of ferrocenyl methyl ester #15

Closed KlementineJBS closed 2 years ago

KlementineJBS commented 2 years ago

Link to HIRAC and master page.

Next attempt is #18

Ferrocenylmethanol synthesis .docx

Reaction Scheme

Reduction of ferrocenyl methyl ester

Outcome

332 mg (1.54 mmol), 95%

Ready to carry through to azidation.

Notes

KlementineJBS commented 2 years ago

22.06.22

  1. Set up a dry 50 mL 2-neck flask under N2
  2. Added KBS14 (396 mg, 1.62 mmol) by solution transfer (10 mL dry THF)
  3. Added LiAlH4 (2.0 mL, 1 M in THF, 2 mmol, 1.23 equiv.)
  4. Left stirring from 11.05 am
  5. TLC'd at 2 pm - indicated completion. Unsure of what produces secondary spot in SM - presumed to be decomposition from SM sample (which was > 1 year old).

30:70 ethyl acetate:pet benz

  1. Quenched with ethyl acetate (15 mL) and poured over Rochelle's salts (40 mL, sat.) to co-ordinate Al salts
  2. Extracted with ethyl acetate (4 x 40 mL). Drained light-coloured emulsion into aqueous each time
  3. Washed with brine (100 mL)
  4. Dried over MgSO4 and rotovapped

Vial (empty) = 15.5814 Vial (full) = 15.9132 Mass = 331.8 mg

NMR

1H NMR (300 MHz, CDCl3) δ 4.33 (s, 2H), 4.24 (t, 2H), 4.18 (m, 7H)

KBS15-5 cr_1.zip

KBS15-5 cr processed.pdf

Some residual ethyl acetate but otherwise mostly clean.