Thiazole → 8-(1,3-Thiazol-2-yl)-1,4-dioxaspiro[4.5]decan-8-ol

Participants

Reaction Conditions

Reaction Steps

Thiazole (25.02 mL, 352 mmol) was diluted with THF (300 mL) and cooled to −78° C. n-BuLi (1.6 M, 220 mL, 532 mmol) was added at such a rate that the internal temperature did not exceed −65° C. The mixture was aged for 20 min, then 1,4-dioxaspiro[4.5]decan-8-one (50 g, 320 mmol) was added as a solution in THF (420 mL) drop wise via addition funnel. The mixture was stirred for 2 h and then quenched with water. The flask was removed from the cooling bath and stirred until it reached 0° C. The mixture was transferred to a separatory funnel with EtOAc and brine and then extracted with EtOAc. The combined organics were dried with MgSO4, filtered and concentrated to an orange viscous oil. The oil was diluted with EtOAc and concentrated to ˜100 mL. A stir bar was added to the flask and hexanes was added drop wise via addition funnel. The mixture was stirred for 1 h then cooled to −10° C. and filtered. The filtrate was washed with hexanes (2×) and dried to afforded 8-(1,3-thiazol-2-yl)-1,4-dioxaspiro[4.5]decan-8-ol (66 g, 274 mmol, 85% yield).

Provenance & Evidence