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Synthesis of 2-methyl-3-hydroxy-4H-pyran-4-one and 4-hydroxy-5-methyl-2H-furan-3-one from carbohydrates

✍ Scribed by Shono, Tatsuya; Matsumura, Yoshihiro; Hamaguchi, Hiroshi; Naitoh, Shigeki


Book ID
121236706
Publisher
American Chemical Society
Year
1983
Tongue
English
Weight
434 KB
Volume
48
Category
Article
ISSN
0022-3263

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The crystal structure of the racemic title compound, C~12~H~12~O~3~, allowed the determination of the relative configuration at the two stereogenic centers. For the __R,R__ isomer, the O—C—C—O and C—C—C—C torsion angles around the bond between the two methine C atoms are 62.38 (15) and −175.49 (13)°

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## Abstract Phenylhydrazine or hydrazine react with 3‐acetyl‐4‐hydroxy‐6‐methyl‐2__H__‐pyran‐2‐one (1) to give 4‐acetoacetyl‐3‐methylpyrazolin‐5‐ones 4. The synthesis of bipyrazoles and pyrazoloisoxazoles from 4 are reported.