反应详情

A 31.3 g. (0.115 M) quantity of dl-trans-3-amino-4-hydroxycyclopentene toluenesulfonate is dissolved in 240 ml. of tetrahydrofuran and 47 ml. (0.46 M) of triethylamine. The resultant stirred solution is cooled to 5° and treated dropwise with 22.8 g. (0.115 M) of o-methoxycarbonylbenzoylchloride. The reaction is then allowed to warm to 25°. After 48 hours the reaction is partitioned between Ethyl acetate and water. The ethyl acetate layer is dried over magnesium sulfate and concentrated in vacuo leaving 29.6 g. of residue. This residue is chromatographed over silica gel 60 eluted with 5 l. of (10-90) and 7.5 l. of (20-80) acetone-methylene chloride. Three hundred ml. fractions are collected. The product is isolated in fractions 25-35, which upon standing crystallizes to yield 14.2 g. of dl-trans-4-hydroxy-3-phthalido-cyclopentene, m.p. 114°-116°.

1. temperatureis cooled to 5°
2. additiontreated dropwise with 22.8 g
3. temperatureto warm to 25°
4. customAfter 48 hours the reaction is partitioned between Ethyl acetate and water
5. dry with materialThe ethyl acetate layer is dried over magnesium sulfate
6. concentrationconcentrated in vacuo
7. customleaving 29.6 g
8. customThis residue is chromatographed over silica gel 60
9. washeluted with 5 l
10. customfractions are collected
11. customThe product is isolated in fractions 25-35, which
12. customupon standing crystallizes
13. customto yield 14.2 g