Tetrahydrofuran → HCID 66879181, compound

Participants

Reaction Steps

To a solution of tetrahydro-2H-thiopyran-4-carboxylic acid (2.0 g, 13.7 mmol) in THF (25 mL) was added CDI (2.66 g, 1.20 eq). The mixture was stirred at rt for 1 h. To a solution of LiHMDS (1.0 M in THF, 29 mL) in THF (30 mL) at −78° C. was added EtOAc (2.90 mL) dropwise. The mixture was stirred at −78° C. for 1 h, then the acid/CDI mixture was added through an addition funnel over 30 min at −78° C. The mixture was stirred at −78° C. for 1 h then allowed to warm up to rt over 2 h. The reaction was quenched with saturated NH4Cl and extracted with diethyl ether. The combined organic layers were dried over Na2SO4, filtered and concentrated. The residue was purified by Biotage (CH2Cl2/EtOAc, 100:1 to 10:1) to give the title compound as a clear oil. LC/MS RT=1.73 min (5 min method). Mass calculated for, M+H 217.08, observed 217.08.

Provenance & Evidence