KBS15-5 - Reduction of ferrocenyl methyl ester

[KlementineJBS]

Link to HIRAC and master page.

Next attempt is #18

Ferrocenylmethanol synthesis .docx

Reaction Scheme

Outcome

332 mg (1.54 mmol), 95%

Ready to carry through to azidation.

Notes

[KlementineJBS]

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

7. Quenched with ethyl acetate (15 mL) and poured over Rochelle's salts (40 mL, sat.) to co-ordinate Al salts
8. Extracted with ethyl acetate (4 x 40 mL). Drained light-coloured emulsion into aqueous each time
9. Washed with brine (100 mL)
10. 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.