Ferrocenecarboxylic acid, cas is 1271-42-7, it is a common heterocyclic compound, the iron-catalyst compound, its synthesis route is as follows.,1271-42-7
To a suspension of ferrocenylcarboxylic acid (60 mg, 0.26 mmol,3 equiv) in 1 mL of dry CH2Cl2 was added at room temperatureoxalyl chloride (225 mL, 2.65 mmol, 27 equiv). After 30 min at roomtemperature, the solution took a deep red color. The mixture wasconcentrated in vaccuo to remove excess oxalyl chloride. Podophyllotoxin(38 mg, 90 mmol, 1 equiv) was solubilizedequiv in1.5 mL of dry CH2Cl2 and Et3N (15 mL, 0.11 mmol, 1.2 equiv) wasadded. To this mixture was added at 0 C ferrocenoyl chloride in2 mL of CH2Cl2. Then a few crystals of DMAP were added and themixture was stirred at 0 C for 30 min and at room temperature for1 h. Reaction was quenched by addition of water, extracted withCH2Cl2 (3), washed with diluted HCl (~0.1 N), dried over MgSO4and concentrated under vacuum. The crude product was purifiedby preparative TLC on silica (AcOEt/Cyclohexane 2/3) to yield 35 mgof the desired compound as an orange powder (60%). 1H NMR(400 MHz, CDCl3): delta (ppm) 6.90 (s, 1H), 6.58 (s, 1H), 6.44 (s, 2H),6.04-5.97 (m, 3H), 4.85 (dt, J = 2.5, 1.3 Hz, 1H), 4.81 (dt, J= 2.5,1.3 Hz, 1H), 4.64 (d, J= 4.3 Hz, 1H) 4.50-4.44 (m, 3H), 4.30 (m, 1H),4.25 (s, 5H), 3.81 (s, 3H), 3.80 (s, 6H), 3.02e2.87 (m, 2H). 13C NMR(101 MHz, CDCl3): delta (ppm) 173.8, 172.6, 152.8, 148.3, 147,8, 137.4,135.1, 132.5, 129.0, 109.9, 108.4, 107.1, 101.8, 73.5, 72.1, 72.0, 71.8,70.4, 70.3, 70.0, 61.0, 56.3, 45.8, 43.9, 39.1. IR (neat, cm-1): 1780,1711, 1485, 1240, 1128. Exact mass (C33H30FeO9): calculated649.1132 (M +Na)+, measured 649.1121.
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Reference£º
Article; Beauperin, Matthieu; Polat, Dilan; Roudesly, Fares; Top, Siden; Vessieres, Anne; Oble, Julie; Jaouen, Gerard; Poli, Giovanni; Journal of Organometallic Chemistry; vol. 839; (2017); p. 83 – 90;,
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