反应详情

Cool a THF (50 mL) solution of 9,10-dihydroanthracene (5.10 g, 28 mmol) to 0° C. and add 1.6M n-BuLi (19 mL, 30 mmol) slowly. After 30 minutes, add m-anisaldehyde (3.4 mL, 28 mmol) to the dark brown solution. Allow the reaction to slowly warm to ambient temperature and then carefully quench with aqueous saturated NH4Cl. Shake the entire reaction with water/EtOAc and dry the organic layer (MgSO4). Concentrate under reduced pressure to give 9.4 g light tan oil. Purify by column chromatography using 25% EtOAc/hexane to give 4.7 g (53%) as a colorless oil that rapidly crystallized, mp 105.9° C. HPLC shows 94% purity.

1. customthe reaction
2. customcarefully quench with aqueous saturated NH4Cl
3. customShake the entire reaction with water/EtOAc
4. dry with materialdry the organic layer (MgSO4)
5. concentrationConcentrate under reduced pressure
6. customto give 9.4 g light tan oil
7. customPurify by column chromatography
8. customto give 4.7 g (53%) as a colorless oil
9. customthat rapidly crystallized