The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: (R)-4-Hydroxydihydrofuran-2(3H)-one( cas:58081-05-3 ) is researched.Application In Synthesis of (R)-4-Hydroxydihydrofuran-2(3H)-one.Tanaka, Akira; Yamashita, Kyohei published the article 《A novel synthesis of (R)- and (S)-4-hydroxytetrahydrofuran-2-ones》 about this compound( cas:58081-05-3 ) in Synthesis. Keywords: furanone hydro hydroxy chiral; hydroxy lactone chiral; butanolide hydroxy chiral; dioxolaneacetate methyl; dioxaspirodecaneacetate chiral; spirodioxadecaneacetate chiral. Let’s learn more about this compound (cas:58081-05-3).
The hydroxy ester I (R = H, R1 = OH), prepared from L-ascorbic acid by sequential treatment with acetone and AcCl, 30% H2O2 and CaCO3, and Me2SO4, was treated with MeSO2Cl and pyridine in CH2Cl2 to give 90% I (R = H, R1 = MeSO3), which, when heated at 85° with LiCl in DMF furnished a mixture of the erythro and threo chloro esters I (R = Cl, R1 = H; R = H, R1 = Cl) (II). Upon hydrogenolysis with 10% Pd/C in the presence of Et3N, II yielded the ester I (R = R1 = H), which was treated with dilute HCl giving a nearly quant. yield of hydroxylactone III. The (S)-enantiomer was analogously prepd from D-isoascorbic acid.
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Reference:
Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem