反应详情

Thionyl chloride (50 mL) is added to the title B compound, 4-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-benzenesulfonic acid sodium salt (18.1 g, 52.46 mmol) at 0° C. After 10 min, the ice bath is removed and the mixture is stirred at RT for 30 min. An additional 50 mL of thionyl chloride is added, followed by about 1 mL of DMF. The solid dissolves within 10 min. Stirring is continued for an additional 2.5 h and the mixture is then concentrated under vacuum. The resulting yellow solid is partitioned between 250 mL of water and 250 mL of EtOAc (warm). The organic layer is further washed with water (3×250 mL), 0.1 N aqueous NaOH (4×250 mL) and brine (1×250 mL). The organic phase is dried over anhydrous magnesium sulfate, filtered and concentrated under vacuum to give 4-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-benzenesulfonyl chloride as a yellow solid: ESI-MS 363.99 [M+1]+.

1. customthe ice bath is removed
2. additionAn additional 50 mL of thionyl chloride is added
3. dissolutionThe solid dissolves within 10 min
4. stirringStirring
5. waitis continued for an additional 2.5 h
6. concentrationthe mixture is then concentrated under vacuum
7. customThe resulting yellow solid is partitioned between 250 mL of water and 250 mL of EtOAc (warm)
8. washThe organic layer is further washed with water (3×250 mL), 0.1 N aqueous NaOH (4×250 mL) and brine (1×250 mL)
9. dry with materialThe organic phase is dried over anhydrous magnesium sulfate
10. filtrationfiltered
11. concentrationconcentrated under vacuum