反应详情

To a mixture of 3-(prop-2-en-1-yl)quinoline-2,4-diol (4.0 g), triphenylphosphine (6.78 g) and benzyl alcohol (2.27 ml) in THF (240 ml) at 0° C. was added dropwise a THF (12 mL) solution of diisopropylazodicarboxylate (5.02 ml). Upon completion of addition, the mixture was allowed to stir at room temperature for 60 minutes. The reaction mixture was concentrated in vacuo to give a thick oil. Oil dissolved in DCM (20 mL) and solids started to precipitate. The solids were filtered and washed with DCM (10 mL). This provided 2.0 g of the desired product. Purification of the mother liquors using flash chromatography (ISCO, 1-8% acetone/DCM) gave an oil that was a mixture of products. This oil was dissolved in 15 mL of diethyl ether and seeded with the desired product. The mixture was stirred overnight and crystallization occurred. The solids were filtered and washed with ether to provide the desired product (1.06 g) as a white solid for a total of 3.06 g of product. LRMS (ES+) M/Z (M+H)+ 292.1.

1. additionUpon completion of addition
2. concentrationThe reaction mixture was concentrated in vacuo
3. customto give a thick oil
4. customto precipitate
5. filtrationThe solids were filtered
6. washwashed with DCM (10 mL)
7. customPurification of the mother liquors
8. customgave an oil that
9. additiona mixture of products