Iodine → HCID 11348633, compound

Participants

Reaction Steps

To a solution of 5-(tert-butoxycarbonyl)-4-ethyl-2-formyl-1H-pyrrole-3-carboxylic acid (0.548 g, 2.05 mmol) in CH2Cl2 (8.30 mL) was added a solution of NaHCO3 (0.691 g, 8.21 mmol) water (8.2 mL). The mixture was stirred vigorously during the addition of a solution of KI (1.021 g, 6.15 mmol) and I2 (0.570 g, 2.23 mmol) in water (11.15 mL). The resultant mixture was heated to 45° C. for 60 min until the initial red/brown color faded. The reaction was cooled to ambient temperature and quenched with saturated aqueous Na2SO3 (25 ml) prior to separation of the phases. The aqueous layer was extracted with CH2Cl2 (1×30 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated. The resultant residue was purified by normal phase chromatography (10-30% ethyl acetate/hexanes). Proton NMR for the product was consistent with the title compound. 1H NMR (500 MHz, CD3OD) δ 9.59 (s, 1H); 2.77 (q, J=7.6 Hz, 2H); 1.60 (s, 9H); 1.10 (t, J=7.6 Hz, 3H). HRMS (ES) exact mass calculated for C12H16INNaO3 (M+Na+): 372.0072. Found 372.0067.

Provenance & Evidence