HRID1382533

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID176

Acetic Acid

C2H4O2

HCID24636

Cerium trichloride

CeCl3

HCID4311764

Sodium borohydride (Na(BH4))

H4BNa

$结构：CCCCC(C)(C)C(=O)/C=C/[C@@H]1[C@@H](C/C=C\CCCC(=O)OC)[C@H](Cl)C[C@H]1O.CCCCC=CC(=O)OC$

HCID86742756

未命名化合物

PRODUCTS

生成物

$结构：CCCCC(C)(C)[C@H](O)/C=C/[C@@H]1[C@@H](C/C=C\CCCC(=O)OC)[C@H](Cl)C[C@H]1O$

HCID13853250

Methyl (5Z,9β,11α,13E,15R)-9-chloro-11,15-dihydroxy-16,16-dimethylprosta-5,13-dien-1-oate

C23H39ClO4

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID887

Methanol

CH4O

PROCEDURE

实验过程

A solution of 600 mg of IX in 25 ml of methanol is mixed with 60 mg of cerium(III) chloride with stirring and then 500 mg of sodium borohydride is added at -40° C. After 1 hour, thin-film chromatography checking shows a complete reduction. It is installed with 1 ml of glacial acetic acid, concentrated by evaporation in a vacuum, diluted with water and extracted several times with dichloromethane. The combined organic phases are washed with sodium bicarbonate solution and salt water, dried over magnesium sulfate and concentrated by evaporation in a vacuum. The residue is chromatographed on silica gel with dichloromethane/1-10% acetane. First 280 mg of XI is eluted as nonpolar component and then 295 mg of the desired epimer X, both as colorless oils.

WORKUP

后处理

concentrationconcentrated by evaporation in a vacuum
additiondiluted with water
extractionextracted several times with dichloromethane
washThe combined organic phases are washed with sodium bicarbonate solution and salt water
dry with materialdried over magnesium sulfate
concentrationconcentrated by evaporation in a vacuum
customThe residue is chromatographed on silica gel with dichloromethane/1-10% acetane
washFirst 280 mg of XI is eluted as nonpolar component