Methyl iodide → HCID 178500945, compound

Participants

Reaction Steps

An ice-cooled solution of intermediate D19 (17.1 g) in THF (450 ml) was stirred under an atmosphere of N2. NaOtBu (1 eq) was added and after 30 minutes a solution of iodomethane (3.15 ml) in THF was added dropwise. After another 30 minutes an additional NaOtBu (1 eq) was added and the contents stirred at ˜0° C. When the reaction was completed after 45 minutes, a saturated solution of NH4Cl was added and the reaction was diluted with EtOAc. The phases were separated and the aqueous phase extracted with EtOAc (×2). The combined organic extracts were washed with brine, then dried (Na2SO4). Filtration and concentration under reduced pressure gave the crude material as an amber oil. Yield: 17.2 g of intermediate D20 (59%).

Provenance & Evidence