Tetrahydrofuran → HCID 58000830, compound

Participants

Reaction Steps

The intermediate from Example 1 Step E (1.76 g, 3.99 mmol) was suspended in 150 mL THF and the flask was immersed in a room temperature water bath followed by the addition 11 mL (2.7 equiv) of a 1M solution of potassium tert-butoxide (in THF). After 45 minutes, 1.79 g of SEMCl (2.7 equiv) was added. The reaction was allowed to warm to ambient temperature overnight. The volatiles were removed in vacuo and the crude residue was dissolved in EtOAc and washed sequentially with a saturated solution of NaHCO3 and brine. The solution was dried with MgSO4 and filtered. Evaporation of the solvent under reduced pressure provided the crude residue that was purified on silica gel (gradient elution from 0 to 30% EtOAc/hexanes).

Provenance & Evidence