反应详情

A solution of triethyl citrate (34.1 g, 123 mmol) in ethanol and water (30 ml) is treated with sodium hydroxide (3.70 g, 92.6 mmol) and stirred at room temperature under argon for 4.5 hours. The reaction mixture is concentrated on a rotary evaporator then diluted with water (50 ml). The pH is adjusted to ca. 1 using 2N HCl. The aqueous solution is then extracted with a large excess of chloroform (4×150 ml). The combined organic layers are dried (MgSO4), filtered and concentrated to give crude oil. Purification by flash chromatography (5% MeOH/CH2Cl2 to 1% AcOH/5%MeOH/CH2Cl2) gives 8.72 g of product (38% as a racemate.

1. concentrationThe reaction mixture is concentrated on a rotary evaporator
2. additionthen diluted with water (50 ml)
3. extractionThe aqueous solution is then extracted with a large excess of chloroform (4×150 ml)
4. dry with materialThe combined organic layers are dried (MgSO4)
5. filtrationfiltered
6. concentrationconcentrated
7. customto give crude oil
8. customPurification by flash chromatography (5% MeOH/CH2Cl2 to 1% AcOH/5%MeOH/CH2Cl2)