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KBS15: Reduction to ferrocenylmethanol
(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%).
40:60 EtOAc/hexane, UV
H NMR, 300 MHz, CDCl3
KBS15-1 clean (3.96 - 4.40 zoom).pdf
Peaks at 4.11 (m, 7H), 4.17 (t, 2H), 4.26 (d, 2H)
KBS15-1 - 44%
KBS15-2 - 101%, some residual solvent
KBS15-3 - 54%
KBS15-4 - 98%, some residual water
KBS15-5 - 95%, traces of ethyl acetate
KBS15-6 - 104%, traces of ethyl acetate