反应详情

温度

0 °C

To a mixture of 5-hydroxy-2,2-dimethyl-benzo[1,3]dioxin-4-one (Uchiyama M. et al Org. Lett. 2006, 8(24), 5517-5520) (2.0 g, 10.4 mmol) and benzyl bromide (1.78 g, 10.4 mmol) in DMF in an ice bath was added sodium hydride (60% dispersed in mineral oil, 624 mg, 15.6 mmol). Resulting mixture was stirred at 0° C. for 10 min and then at rt for 6 h. Reaction mixture was quenched with water (250 mL), neutralized using 1 N HCl to pH=6-7 and extracted with EtOAc (2×). Combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated. Crude product was triturated with hexanes (50 mL). Solid was collected and dried in vacuo to provide the title compound 2.5 g. 1H NMR (200 MHz, CDCl3): δ (ppm)=7.54 (m, 2H), 7.37 (m, 4H), 6.57 (m, 2H), 5.25 (s, 2H), 1.71 (s, 6H).

1. customResulting mixture
2. waitat rt for 6 h
3. customReaction mixture
4. customwas quenched with water (250 mL)
5. extractionextracted with EtOAc (2×)
6. washCombined organic layers were washed with brine
7. dry with materialdried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated
10. customCrude product was triturated with hexanes (50 mL)
11. customSolid was collected
12. customdried in vacuo