Tributylstannane → HCID 86725327, compound

Participants

Reaction Conditions

Reaction Steps

Into a 500 ml flask, the product from step (b) (15.2 mmol) dissolved in toluene (100 ml) was placed. The flask was purged with Ar, followed by the addition of tributyltin hydride (8.36 ml, 31.11 mmol). The reaction mixture was placed in a pre-heated (110° C.) oil bath and stirred for 20 minutes. The reaction mixture was cooled, quenched with saturated aqueous Na2CO3, and extracted with EtOAc (3×). The combined EtOAc extracts were washed with brine, dried over Na2SO4, and solvent evaporated in vacuo to give the crude product. Purification by silica-gel chromatography (gradient elution: 0 to 15% DCM w/20% MeOH, 1% NH4OH in DCM:) gave the sub-title compound as a yellow oil (3.7 g). 1H NMR (300 MHz, CDCl3) δ 8.54-8.52 (m, 1H); 8.37-8.33 (m, 1H); 7.23-7.21 (m, 2H); 7.15-7.09 (m, 2H); 4.67 (d, J=19.2, 1H); 4.14-4.08 (m, 2H); 3.69-3.60 (m, 1H); 3.53-3.48 (m, 2H); 3.42-3.34 (m, 2H); 3.21-3.10 (m, 1H); 2.92-2.87 (m, 2H); 2.65-2.58 (m, 1H); 2.52-2.44 (m, 1H); 1.32-1.20 (m, 3H); MS: ESI (positive): 373 (M+1).

Provenance & Evidence