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Straight and versatile synthesis of substituted perhydrofuro[2,3-b]pyrans from 2-chloromethyl-3-(2-methoxyethoxy)propene

✍ Scribed by Francisco Alonso; Emilio Lorenzo; Jaisiel Meléndez; Miguel Yus

Book ID
104205444
Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
291 KB
Volume
59
Category
Article
ISSN
0040-4020

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✦ Synopsis

The reaction of 2-chloromethyl-3-(2-methoxyethoxy)propene with an excess of lithium powder and a catalytic amount of naphthalene (2.5%) in the presence of a carbonyl compound (E 1 ¼R 1 R 2 CO) in THF at 278 to 08C, followed by the addition of an epoxide [E 2 ¼R 3 R 4 C(O)CHR 5 ] at 0 to 208C leads, after hydrolysis, to the expected methylidenic diols. These diols when subjected to successive hydroboration -oxidation and further oxidation, spontaneous cyclization occurs to furnish a series of differently substituted perhydrofuro [2,3-b]pyrans.

📜 SIMILAR VOLUMES

Substituted perhydrofuropyrans: easy pre
Substituted perhydrofuropyrans: easy preparation from 2-chloromethyl-3-(2-methoxyethoxy)propene through 3-methylene-1,6-diols
✍ Emilio Lorenzo; Francisco Alonso; Miguel Yus 📂 Article 📅 2000 🏛 Elsevier Science 🌐 French ⚖ 184 KB

The reaction of 2-chloromethyl-3-(2-methoxyethoxy)prop-1-ene (1) with an excess of lithium powder and a catalytic amount of naphthalene (2.5%) in the presence of a carbonyl compound (E 1 =R 1 R 2 CO) in THF at -78 to 0°C, followed by treatment with an epoxide [E 2 =R 3 R 4 C(O)CHR 5 ] at 0 to 20°C l