Sodium Bicarbonate → 2-Thiophenemethanol, 5-(3-pyridinyl)-

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Reaction Steps

To a solution of 13 (116 mg, 0.61 mmol) in CH3OH (5 mL) was added sodium borohydride (23 mg, 0.61 mmol) in one portion. The resultant solution was stirred at room temperature for 10 min, stopped by the addition of aqueous sodium bicarbonate (50:50 satd. soln./water, v:v) and the solvent was removed in vacuo. The residue was partitioned between water (50 mL) and EtOAc (50 mL). The organic layer was collected and the aqueous was extracted with EtOAc (2×50 mL). The combined organic extracts were dried (MgSO4) and the solvent was removed in vacuo to afford the title compound 44 (116 mg, 99% yield) as an off white solid: mp=89-90° C.; 1H NMR (CDCl3) δ 8.82 (m, 1H), 8.49 (m, 1H), 7.84 (m, 1H), 7.31 (m, 1H), 7.22 (d, J=4.1 Hz, 1H), 7.01 (d, J=4.1 Hz, 1H), 4.85 (s, 2H); LRMS (ESI) m/z calcd for C11H10NOS [M+H]+ 192. found 192; HRMS (ESI) m/z calcd for C10H10NOS [M+H]+ 192.0483. found 192.0476; HPLC>99% (tR=10.18 min, 55 (A):45 (B) 0.009 (C); tR=3.52 min, 55 (A):45 (B) 0.1 (C)).

Provenance & Evidence