反应详情

温度

0 °C

To a solution of thionyl chloride (8.0 mL) and 2 drops of N,N-dimethylformamide stirring under nitrogen at 0° C. is added the title B compound, 4-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-benzenesulfonic acid sodium salt (1.42 g, 3.8 mmol) in one portion. The resulting suspension is stirred at 0° C. for 10 minutes. The ice bath is removed and the suspension is stirred at room temperature for 1.5 hours. Three more drops of N,N-dimethyl-formamide is added, after which a clear solution results upon stirring for an additional hour. The solution is concentrated under vacuo to a solid residue. The residue is partitioned between water (20 mL) and ethyl acetate (20 mL). The organic layer is separated and washed successively with water (3×20 mL), 0.1N aqueous sodium hydroxide (3×20 mL) and brine (20 mL). The organic layer is dried over anhydrous MgSO4, filtered and concentrated in vacuo to give an oil which slowly solidifies to give 0.48 g of 4-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-benzenesulfonyl chloride: [M+1]+=363.99.

1. customThe ice bath is removed
2. stirringthe suspension is stirred at room temperature for 1.5 hours
3. additionThree more drops of N,N-dimethyl-formamide is added
4. customafter which a clear solution results
5. stirringupon stirring for an additional hour
6. concentrationThe solution is concentrated under vacuo to a solid residue
7. customThe residue is partitioned between water (20 mL) and ethyl acetate (20 mL)
8. customThe organic layer is separated
9. washwashed successively with water (3×20 mL), 0.1N aqueous sodium hydroxide (3×20 mL) and brine (20 mL)
10. dry with materialThe organic layer is dried over anhydrous MgSO4
11. filtrationfiltered
12. concentrationconcentrated in vacuo
13. customto give an oil which