Ethyl benzo[d]thiazole-6-carboxylate → 6-(Hydroxymethyl)benzothiazole

Participants

Reaction Steps

To a suspension of 76 mg of LiAlH4 in dry THF (20 mL) under N2 was added dropwise and at 0° C. a solution of ester 39 (207 mg, 1 mmol) in dry THF (6.7 ml). After 2 h. the ice bath was removed and the mixture was stirred overnight at room temperature, then cooled to 0° C. The excess of LiAlH4 was destroyed very cautiously by a saturated solution of NH4Cl. The organic layer was removed and the aqueous layer was extracted with EtOAc. The combined organic extracts were dried (Na2CO3) and evaporated, obtaining an orange oil that was purified by column chromatography, eluting with EtOAc/MeOH (90/10). 1H NMR (CD3OD): δ 9.20 (s, 1H), 8.02 (m, 2H), 7.53 (d, 1H, J=8.04 Hz), 4.76 (s, 2H).

Provenance & Evidence