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

Participants

Reaction Conditions

Reaction Steps

Thiazole (25.0 mL, 352 mmol) was diluted with THF (300 mL) and cooled to −780° C. n-BuLi (220 mL, 352 mmol) was added at such a rate that the internal temperature did not exceed −65 C. A yellow slurry formed and the addition took 40 min. The reaction 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) dropwise via addition funnel. After 2 h, the reaction was quenched with water, the cooling bath removed and the mixture stirred until the internal temperature reached 0° C. The mixture was diluted with EtOAc and the layers were separated followed by extraction of the aqueous portion with EtOAc. The combined organics were dried with MgSO4, filtered, and concentrated to a viscous orange oil. EtOAc was added and concentrated to 100 mL. Hexanes was added dropwise via an addition funnel. The mixture was stirred for 1 h then cooled to −10° C. and filtered. The white cake was washed with hexanes (2×) then dried under a nitrogen bag to afford 8-(1,3-thiazol-2-yl)-1,4-dioxaspiro[4.5]decan-8-ol (66 g, 85%) as a white solid.

Provenance & Evidence