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Synthesis 2023; 55(17): 2670-2673
DOI: 10.1055/a-2088-1624
DOI: 10.1055/a-2088-1624
psp
Practical Synthesis of Pent-4-yn-1-ol and Pent-4-en-1-ol from Tetrahydrofurfuryl Halides
Abstract
Pent-4-yn-1-ol was prepared in a high yield by the reaction of tetrahydrofurfuryl chloride with n-BuLi in t-BuOMe at 0 °C. Pent-4-en-1-ol was prepared in a high yield by either the reaction of tetrahydrofurfuryl chloride or tetrahydrofurfuryl bromide with lithium in tetrahydrofuran at temperatures from 0 °C to ambient temperature.
Key words
pent-4-yn-1-ol - tetrahydrofurfuryl chloride - n-butyllithium - t-butyl methyl ether - pent-4-en-1-ol - tetrahydrofurfuryl bromide - lithium - tetrahydrofuranPublikationsverlauf
Eingereicht: 25. März 2023
Angenommen nach Revision: 05. Mai 2023
Accepted Manuscript online:
05. Mai 2023
Artikel online veröffentlicht:
05. Juni 2023
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References
- 1a Corley EG, Thompson AS, Huntington MF. Org. Synth. 2000; 77: 231
- 1b Thompson AS, Corley EG, Huntington MF, Grabowski JJ. Tetrahedron Lett. 1995; 36: 8937
- 1c Thompson AS, Corley EG, Huntington MF, Grabowski JJ, Remenar JF, Collum DB. J. Am. Chem. Soc. 1998; 120: 2028
- 2a Jones ER. H, Eglinton G, Whiting MC. Org. Synth. 1953; 33: 68
- 2b Eglinton G, Jones ER. H, Whiting MC. J. Chem. Soc. 1952; 2873
- 2c Matovic N, Matthias A, Gertsch J, Raduner S, Bone KM, Lehman RP, DeVoss JJ. Org. Biomol. Chem. 2007; 5: 169
- 2d Zhdanko A, Maier ME. Eur. J. Org. Chem. 2014; 79: 3411
- 3 Zhou X. Chinese Patent 101830778, 2010 ; Chem. Abstr. 2010, 153, 456201
- 4 Graduate Lecture Organic Chemistry I, 2nd ed. Noyori R. Tokyo Kagaku Dojin; Tokyo: 2019: 311
- 5 Stanetty P, Mihovilovic MD. J. Org. Chem. 1997; 62: 1514
- 6 Kagan HB, Namy JL, Girard P. Tetrahedron 1981; 37 (Suppl. 01) 175
- 7 Paul R. Bull. Soc. Chim. Fr. 1935; 2: 745
- 8a Brooks LA, Synder HR. Org. Synth. 1945; 25: 84
- 8b Paul R, Normant H. Bull. Soc. Chim. Fr. 1943; 10: 484
- 8c Gaubert P, Linstead RP, Rydon HN. J. Chem. Soc. 1937; 1971
- 8d Eglinton G, Jones ER. H, Whiting MC. J. Chem. Soc. 1952; 2873
- 9 Sahner JH, Sucipto H, Wenzel SC, Groh M, Hartmann RW, Müller R. ChemBioChem 2015; 16: 946
- 10 Mitsudome T, Takahashi Y, Ichikawa S, Mizugaki T, Jitsukawa K, Kaneda K. Angew. Chem. Int. Ed. 2013; 52: 1481