Name is Ferrocenecarboxaldehyde, as a common heterocyclic compound, it belongs to iron-catalyst compound, and cas is 12093-10-6, its synthesis route is as follows.,12093-10-6
To a round bottomed flask equipped with a magnetic stirrer bar was added ferrocene carboxaldehyde(535 mg, 2.5 mmol, 1 eq). The flask was then charged with ethanol (4 cm3) and THF (1 cm3). Thered solution was then treated with sodium borohydride (123 mg, 3.2 mmol, 1.3 eq). The flask wasthen sealed and placed under a nitrogen atmosphere. After 30 minutes the solution had changedcolour to an orange and TLC analysis indicated full consumption of the starting material. The flaskwas then concentrated to 90% of original volume in vacuo. The dark orange residue was then takenup in EtOAc (15 cm3) and NaHCO3 (15 cm3). The bi-phasic mixture was transferred to separatingfunnel, the aqueous layer was separated and then back extracted with EtOAc (3 x 5 cm3), thecombined organic washings were then dried over MgSO4, filtered and then concentrated in vacuo togive a yellow solid. The ferrocene methanol was then taken up in 1,3-propanediol (5 cm3), the yellowsolution was then treated with ytterbium (Ill) triflate (77 mg, 0.125 mmol, 5 mol%). The flask wasthen sealed and heated to 100 C. After heating for 10 minutes TLC analysis indicated fullconsumption of the starting material. The flask was cooled to room temperature, diluted with H20(20 cm3) and EtOAc (20 cm3). The organic layer was then separated and the aqueous layer backextracted with EtOAc (3 x 5 cm3). The combined organic layers were then washed with H20 (2018 cm3) and brine (sat) (20 cm3) then dried over MgSO4, filtered then concentrated in vacuo to give an orange solid. Purification was then carried out by silica-gel chromatography eluting with n-Hex 1:1 EtOAc to give the desired product 3-(ferrocenyloxy)propan-lol (1) as an orange powder (514 mg, 74%).?H NIVIR (250 MHz, CDC13); oH: 4.24 (s, 4H), 4.11 (s, 6H), 3.65 (t, 2H, J 5.4 Hz), 3.54 (t, 2HJ=5.4 Hz), 3.65 (t, 2H J = 5.4 Hz), 2.52 (br s, 1H), 1.7 (quin 2H, J = 5.6 Hz); ?3C NIVIR (75 IVIHz, CDC13); Oc: 83.6, 77.3, 71.5, 69.4, 69.3, 69.2, 68.7, 32.0; HRMS (ESI iTOF) calculated for C,4H,8FeO2Na m/z 297.0553 found 297.0560 (m/z + Na); Electrochemical potential: 181 mV.
With the complex challenges of chemical substances, we look forward to future research findings about Ferrocenecarboxaldehyde
Reference£º
Patent; ATLAS GENETICS LIMITED; MARSH, Barrie J.; FROST, Christopher G.; SHARP, Jonathan; WO2015/52516; (2015); A1;,
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