反应详情

Sodium bis(trimethylsilyl)amide (0.31 ml of a 1.0 M solution in THF, 0.31 mmol) was added to a solution of the aryl amide 103 (100 mg, 0.282 mmol) in THF (1.3 mL) at 0° C. After 15 min a solution of the methyl 7-iodohept-5-ynoate (90 mg, 0.338 mmol) in THF (0.3 mL) was added and the reaction was warmed room temperature. After stirring for 16 h the reaction was the quenched with saturated aqueous ammonium chloride and extracted with EtOAc. The organic portion was washed with brine, dried (MgSO4), filtered and the filtrate was concentrated in vacuo. Purification by FCC (silica gel, 3:2 hex/EtOAc) gave 35 mg (25%) of ester 104.

1. customquenched with saturated aqueous ammonium chloride
2. extractionextracted with EtOAc
3. washThe organic portion was washed with brine
4. dry with materialdried (MgSO4)
5. filtrationfiltered
6. concentrationthe filtrate was concentrated in vacuo
7. customPurification by FCC (silica gel, 3:2 hex/EtOAc)