5-tert-Butyl 2-ethyl 6,7-dihydrothieno[3,2-c]pyridine-2,5(4H)-dicarboxylate → 1,1-Dimethylethyl 6,7-dihydro-2-(hydroxymethyl)thieno[3,2-c]pyridine-5(4H)-carboxylate

Participants

Reaction Steps

Tetrahydrofuran (10 ml) was added dropwise to lithium aluminium hydride (0.46 g, 2 eq.) at 0° C. and the mixture was stirred for 10-15 min at the same temperature. Then a solution of 5-tert-butyl 2-ethyl 6,7-dihydrothieno[3,2-c]pyridine-2,5(4H)-dicarboxylate (2 g, 0.006 mol) in tetrahydrofuran (10 ml) was added dropwise to the mixture at 0° C. and the resulting reaction mixture was stirred for 1-2 h at the same temperature. Progress of the reaction was monitored by TLC (30% ethyl acetate/hexane). Upon completion of the reaction the reaction mixture was poured into ice water and quenched with saturated sodium sulfate solution at 0° C. The mixture was filtered over a bed of Celite and the filtrate was extracted with ethyl acetate (2×150 ml). The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure to yield the crude product as a pale yellow colored liquid. The crude product obtained was directly employed in the next step. Yield: 1.6 g (92%).

Provenance & Evidence