Sodium hydride → HCID 131734769, compound

Participants

Reaction Conditions

Reaction Steps

To a yellow solution of Example 38 (542 mg) in THF (6 mL) was added NaH (62 mg, 60% in mineral oil) at 0° C. The resulting pale yellow foaming suspension was stirred at 0° C. for 15 min under argon, then SEMCl (182 mg) was added and stirring was continued for 1.25 h. The reaction mixture was quenched by addition of water. Phases were separated and the org. layer was washed with water and brine. The aq. layers were extracted twice with EA. The combined org. layers were dried over MgSO4, filtrated off, evaporated and dried in high vacuo. The crude was purified by CC (Biotage, SNAP 25 g cartridge, solvent A: DCM; solvent B: DCM/MeOH 8/2; gradient in % B: 5 for 4CV, 5 to 15 over 6CV, 15 for 3CV) to afford 530 mg of light yellow solid. LC-MS (B): tR=0.91 min; [M+H]+: 652.48.

Provenance & Evidence