2-Furancarboxylicacid,4-cyano-,methylester(9CI) synthesis
- Product Name:2-Furancarboxylicacid,4-cyano-,methylester(9CI)
- CAS Number:357289-65-7
- Molecular formula:C7H5NO3
- Molecular Weight:151.12
58235-80-6
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Yield:357289-65-7 76%
Reaction Conditions:
with tetrakis(triphenylphosphine) palladium(0) in N,N-dimethyl-formamide at 80;Inert atmosphere;
Steps:
2.4 4.2.4 Methyl 4-cyanofuran-2-carboxylate (11)
Methyl 4-bromofuran-2-carboxylate (10, 141 mg, 0.74 mmol), Pd(PPh3)4 (85 mg, 0.07 mmol), and Zn(CN)2 (52 mg, 0.44 mmol) were suspended in anhydrous DMF (5 mL) under an argon atmosphere. The resulting mixture was heated to 80 °C and stirred overnight. After cooling to room temperature the reaction mixture was partitioned between water and diethyl ether. The aqueous layer was extracted with ether (3 * 10 mL). The combined organics were washed with brine (10 mL), dried (Na2SO4), and concentrated under reduced pressure to give a yellow oil, which was chromatographed (ethyl acetate/hexanes, 1:6) to afford a white solid (85 mg, 76%). 1H NMR (500 MHz, CDCl3) δ 8.06 (d, J = 0.9 Hz, 1H), 7.33 (d, J = 0.9 Hz, 1H), 3.94 (s, 3H). 13C NMR (126 MHz, CDCl3) δ 157.59, 151.84, 145.92, 117.76, 111.60, 100.03, 52.69. HRMS (LC-TOF): Calcd for C7H5NO3 151.0269; found 151.0285.
References:
Hawker, Dustin D.;Silverman, Richard B. [Bioorganic and Medicinal Chemistry,2012,vol. 20,# 19,p. 5763 - 5773]
3439-02-9
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2434-03-9
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