KBS15-3 - Synthesis of ferrocenylmethanol

[KlementineJBS]

Synthesis of ferrocenylmethanol

Link to HIRAC and [original method]

Outcome

144 mg (0.666 mmol), 54%

Reaction Scheme

m.w. SM = 244

m.w. product = 216

Method

Ferrocenyl methyl ester (300 mg, 1.23 mmol) was dissolved in anhydrous THF (8 mL) under nitrogen and cooled in an ice bath. LiAlH4 solution (1.90 mL, 1.0 M in THF, 1.90 mmol) was added dropwise and the reaction mixture was refluxed for 1 hour. The mixture was then cooled before ethyl acetate (10 mL) and Rochelle's salts (20 mL) were added with stirring. The mixture was extracted with ethyl acetate (4 x 30 mL), dried over MgSO4 and concentrated under reduced pressure to yield a reddish-orange solid (144 mg, 54%).

Characterisation

NMR

H NMR, 300 MHz, CDCl3

1H NMR (300 MHz, Chloroform-d) δ 4.33 (d, J = 5.6 Hz, 2H), 4.24 (t, J = 1.8 Hz, 2H), 4.18 (d, J = 1.9 Hz, 7H).

Mass Spec

[KlementineJBS]

To consider

[KlementineJBS]

24.06.21

• solution transfer of KBS14 in THF
• refluxed 2.10pm - 3.15 pm
• crude weight = 286.5 mg
• crude NMR: KBS15-3 crude.pdf

[KlementineJBS]

25.06.21

weight = 143.9 mg

KBS15-3 product.pdf

[KlementineJBS]

KBS15-3.pdf