Ethyl (5-bromothiophen-2-yl)(oxo)acetate → Ethyl 2-(5-bromothiophen-2-yl)-2-hydroxyacetate

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 2-(5-bromothiophen-2-yl)-2-oxoacetate (2.5 g, 9.5 mmol) in tetrahydrofuran (50 mL) was added sodium triacetoxy borohydride (2.5 g, 11.8 mmol, 1.2 eq). After stirring for 1 hour at 60° C., the reaction mixture was diluted with ethyl acetate, washed (brine), dried (Na2SO4), filtered and concentrated to provide ethyl 2-(5-bromothiophen-2-yl)-2-hydroxyacetate (2.5 g, 99.24%). 1H NMR (400 MHz, DMSO-d6): δ 1.19 (t, J=7.0 Hz, 3H), 4.11-4.16 (m, 2H), 5.34 (d, J=5.6 Hz, 1H), 6.50 (d, J=6.0 Hz, 1H), 6.91 (d, J=4.0 Hz, 1H), 7.09 (d, J=4.0 Hz, 1H).

Provenance & Evidence