Tetrahydrofuran → Maleic Anhydride
Reaction equation
[H-].[BH3:2].[Na:3].[CH2:4]1[CH2:8][O:7][CH2:6][CH2:5]1.[C:9]1(=[O:14])[O:13][CH2:12][CH:11]=[CH:10]1>CN(C=O)C.C(O)C>[O:7]1[CH:8]=[CH:4][CH:5]=[CH:6]1.[C:12]1(=[O:7])[O:13][C:9](=[O:14])[CH:10]=[CH:11]1.[BH3:2].[Na:3]Participants
Procedure
In general, as a method for obtaining a lactone from an acid anhydride, a method of reducing the acid anhydride using hydride reducing agents is widely known. For example, J. Org. Chem., 35, 3574 (1970) describes a method of synthesizing a lactone compound by applying sodium boron hydride as a reducing agent to various types of cyclic acid anhydride in a THF or DMF solvent. Synthesis, 42 (1974) describes a method of synthesizing γ-crotonolactone, which comprises reducing a cyclic acid anhydride obtained by the Diels-Alder reaction between furan and maleic anhydride with sodium boron hydride in an ethanol solvent, so as to obtain the corresponding lactone. As a method of isolating lactone, the above-described document, J. Org. Chem., 35, 3574 (1970) describes a method which comprises neutralizing the reaction solution obtained by reduction with a hydrochloric acid solution, and then extracting with ether followed by condensation.
Workup
- customSynthesis, 42 (1974)
Sources & evidence
- ORD record
- ord-bf0b4b4aa68b4a3483311a1c8d6a7f40
- Source dataset
- uspto-grants-2006_05
- Patent number
- US07041838B2
Reaction notes
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