Triethylsilane → HCID 14449694, compound
Reaction equation
C([SiH](CC)CC)C.[CH2:8]([O:10][C:11]([C:13]1[NH:14][C:15]([C:18](=O)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:16][CH:17]=1)=[O:12])[CH3:9]>FC(F)(F)C(O)=O>[CH2:8]([O:10][C:11]([C:13]1[NH:14][C:15]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:16][CH:17]=1)=[O:12])[CH3:9]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Triethylsilane (0.323 mL, 2.03 mmol) was added to a stirring, room temperature solution of 5-benzoyl-1H-pyrrole-2-carboxylic acid ethyl ester (29) (0.4180 g, 1.72 mmol) in trifluoroacetic acid (TFA) (4.1 mL, 0.42 M) under N2. After stirring overnight, the reaction did not appear to be complete by HPLC. Addition of addition quantities of triethylsilane did not result in any further changes by HPLC, so the reaction was worked up. The TFA was removed under vacuum, and the crude product was taken up in EtOAc, washed with brine, dried with Na2SO4, filtered, concentrated, and purified by silica gel chromatography (Combiflash column, 98:2 to 95:5 Hexanes:EtOAc) to obtain pure 31 (0.2190 g, 55.6%). 1H (CDCl3, 400 MHz): δ 9.05 (1H, broad s), 7.35-7.28 (2H, m), 7.28-7.23 (1H, m), 7.23-7.18 (2H, m), 6.85 (1H, t, J=3.2 Hz), 6.0 (1H, t, J=3.2 Hz), 4.27 (2H, q, J=7.1 Hz), 4.00 (2H, s), 1.32 (3H, t, J=7.3 Hz) ppm. Partial 13C (CDCl3, 100 MHz): δ 138.51, 136.86, 128.99, 128.88, 126.98, 122.26, 116.08, 109.41, 60.39, 34.37, 14.70 ppm. DEPT (CDCl3, 100 MHz): CH3 carbons: 14.70; CH2 carbons: 60.39, 34.37; CH carbons: 128.99, 128.88, 126.98, 116.08, 109.41 ppm. HPLC: 10.014 min.