反应详情

To a solution of hydroxyl benzaldehyde in DMF was added K2CO3 (2 eq. each hydroxyl group) at 4° C. in an ice-bath and methyl chloromethyl ether (MOM chloride) (1.3 eq. each hydroxyl group). After the solution was stirred at room temperature and monitored by TLC for 3-5 hours, hexanes/dichloromethane (1:1) was added and allowed to stir for 30 min. The solid was filtered out and the filtrate was concentrated. The resulting residue was diluted with EtOAc and washed with H2O twice. The aqueous layer was extracted with EtOAc. The combined organic layers were dried over Na2SO4 and concentrated. The crude was purified by a CombiFlash chromatography system using a Grace silica gel column and hexanes/ethyl acetate (as the eluent) to give MOM protected hydroxylbenzaldehyde. The resulting compound further reacted with excess acetone in ethanol catalyzed by 10% NaOH (1.2 eq. of NaOH). After stirred at room temperature and monitored by TLC for 1-5 hours, the reaction mixture was diluted with CH2Cl2, washed with H2O twice, and extracted with CH2Cl2 twice. The MOM protected hydroxy-phenyl-but-3-en-2-one was obtained after purification by a ConmbiFlash system using hexanes/ethyl acetate as the eluent. The resulting compound reacted with an appropriate MOM protected hydroxybenaldehyde to afford MOM protected hydroxyl 1,5-diphenyl-penta-1,4-dien-3-one, which was deprotected by heating in 50% acetic acid aqueous solution to afford the desired product.

1. stirringto stir for 30 min
2. filtrationThe solid was filtered out
3. concentrationthe filtrate was concentrated
4. additionThe resulting residue was diluted with EtOAc
5. washwashed with H2O twice
6. extractionThe aqueous layer was extracted with EtOAc
7. dry with materialThe combined organic layers were dried over Na2SO4
8. concentrationconcentrated
9. customThe crude was purified by a CombiFlash chromatography system
10. customto give MOM
11. stirringAfter stirred at room temperature
12. waitmonitored by TLC for 1-5 hours
13. washwashed with H2O twice
14. extractionextracted with CH2Cl2 twice
15. customwas obtained
16. customafter purification by a ConmbiFlash system
17. customThe resulting compound reacted with an appropriate MOM