反应详情

温度

-78 °C

BuLi (1.6 M in hexane, 5.70 mL, 9.05 mmol) was added dropwise to a cooled (−78° C.) solution of 2-[2-(tert-butyldimethylsilanyloxy)ethoxymethyl]thiazole (1.900 g, 6.786 mmol) in THF (15 mL). The reaction mixture was stirred at −78° C. for 1 h, and ZnCl2 (1M in THF, 11.3 mL, 11.3 mmol) was added dropwise at −78° C. The cooling bath was removed, and the reaction mixture was stirred for 1 h at rt. A sol. of compound Y (2.00 g, 3.77 mmol) in THF (5 mL) was added dropwise, followed by Pd(PPh3)4 (136 mg, 0.109 mmol). The reaction mixture was stirred at rt for 2 h, partitioned between EtOAc and aq. 1M NaOH, and the layers were separated. The aq. layer was extracted with EtOAc. The combined org. extracts were washed with brine, dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the crude by FC (heptane/EtOAc 7/3) yielded the title compound (1.60 g, 65%) as an orange oil. LC-MS: tR=1.19 min, ES+: 654.33.

1. customThe cooling bath was removed
2. stirringthe reaction mixture was stirred for 1 h at rt
3. stirringThe reaction mixture was stirred at rt for 2 h
4. custompartitioned between EtOAc and aq. 1M NaOH
5. customthe layers were separated
6. extractionThe aq. layer was extracted with EtOAc
7. washextracts were washed with brine
8. dry with materialdried over MgSO4
9. filtrationfiltered
10. customthe solvents were removed under reduced pressure
11. customPurification of the crude by FC (heptane/EtOAc 7/3)