HRID222868

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID9550

Diazomethane

CH2N2

结构：CC1=C[C@H]2[C@@H](CC1)[C@H](C)CC[C@H]2[C@@H](C)C(=O)O

HCID11020893

未命名化合物

PRODUCTS

生成物

结构：CC1=C[C@H]2[C@@H](CC1)[C@H](C)CC[C@H]2[C@@H](C)C=O

HCID10857031

(αR,1R,4R,4aS,8aS)-1,2,3,4,4a,5,6,8a-Octahydro-α,4,7-trimethyl-1-naphthaleneacetaldehyde

C15H24O

收率 48%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID3283

Diethyl Ether

C4H10O

PROCEDURE

实验过程

Dihydroartemisinic aldehyde was synthesized from the isolated dihydroartemisinic acid. The acid was converted to methyl dihydroartemisinate with excess diazomethane in diethyl ether at 0° C. for 5 minutes. The ether and diazomethane were removed under a stream of nitrogen and the methyl ester was reduced to (11R)-dihydroartemisinic alcohol with excess 1.5 M diisobutyl aluminum hydride in toluene at room temperature for 10 min under nitrogen. With subsequent extraction, oxidation to the aldehyde with pyridinium chlorochromate (Corey & Suggs 1975) and purification by HPLC the (11R)-dihydroartemisinic aldehyde was produced at an overall yield of 48% with >99% purity according to GC analysis.

WORKUP

后处理

customThe ether and diazomethane were removed under a stream of nitrogen
extractionWith subsequent extraction, oxidation to the aldehyde
customwith pyridinium chlorochromate (Corey & Suggs 1975) and purification by HPLC the (11R)-dihydroartemisinic aldehyde
customwas produced at an overall yield of 48% with >99% purity