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KBS15: Reduction to ferrocenylmethanol

Klementine Burrell-Sander edited this page May 2, 2023 · 1 revision

Method

(From KBS15-5)

Ferrocenyl methyl ester KBS14 (396 mg, 1.62 mmol) was dissolved in dry THF (10 mL) under nitrogen and LiAlH4 (2.0 mL, 1 M in THF, 2.0 mmol, 1.23 equiv.) was added dropwise. The reaction was stirred for 3 hours before being quenched with ethyl acetate (15 mL) and poured over Rochelle's salts (40 mL, sat.). The mixture was extracted with ethyl acetate (40 mL x 4) and washed with brine (100 mL). The organic extract was dried over MgSO4 and concentrated under reduced pressure to yield a reddish-orange solid (332 mg, 95%).

TLC Conditions

40:60 EtOAc/hexane, UV

Characterisation

NMR

H NMR, 300 MHz, CDCl3

KBS15-1 clean.pdf

KBS15-1 clean (3.96 - 4.40 zoom).pdf

Peaks at 4.11 (m, 7H), 4.17 (t, 2H), 4.26 (d, 2H)

Attempts

Honours

KBS15-1 - 44%

KBS15-2 - 101%, some residual solvent

KBS15-3 - 54%

PhD

KBS15-4 - 98%, some residual water

KBS15-5 - 95%, traces of ethyl acetate

KBS15-6 - 104%, traces of ethyl acetate

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