Convenient preparations of t-butyl esters and ethers from t-butanol

Tetrahedron Letters

Volumn 38, Issue 42, 1997, Pages 7345-7348

  Wright, Stephen W ^a   Hageman, David L ^a   Wright, Ann S ^a   McClure, Lester D ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ESTER; ETHER DERIVATIVE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; IN VITRO STUDY; MASS SPECTROMETRY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

EID: 0030880683     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01792-9     Document Type: Article

References (16)

1. See, for example: (a) Altschul, R. J. Am. Chem. Soc.; 1948, 70, 2569 - 2572
2. (b) Al-Awadi, N. A.; Al-Bashir, R. F.; ElDusouqui, O. M. E. Tetrahedron, 1990, 46, 2903 - 2910
3. (c) Wang, S.-S.; Gisin, B. F.; Winter, D. P.; Makofske, R.; Kulesha, I. D.; Tzougraki, C.; Meienhofer, J. J. Org. Chem., 1977, 42, 1286 - 1290;
4. (d) Pozdnev, V. F. J. Gen. Chem. USSR (Engl. Transl.), 1988, 58, 592 - 597
5. (e) Kim, S.; Lee, J. I. J. Org. Chem., 1984, 49, 1712 - 1716
6. (f) Yamazaki, S. Chemistry Letters, 1995, 127 - 128
7. (g) Widmer, U. Synthesis, 1983, 135 - 136
8. (h) Gibson, F. S.; Bergmeier, S. C.; Rapoport, H. J. Org. Chem., 1994, 59; 3216 - 3218
9. (i) Kamijo, T.; Harada, H.; Iizuka, K. Chem. Pharm. Bull., 1984, 32, 5044 - 5047
10. (j) Dhaon, M. K.; Olsen, R. K.; Ramasamy, K. J. Org. Chem., 1982, 47, 1962 - 1965;
11. (k) Khurana, J. M.; Sahoo, P. K.; Maikap, G. C. Synth. Commun., 1990, 20, 2267 - 2271.
12. See, for example, reference 1a.
13. By contrast, the use of methyl tert-butyl ether under similar conditions has been reported to afford the carboxylic acid methyl ester; see Derevitskaya, V. A.; Klimov, E. M.; Kochetkov, N. K. Tetrahedron Letters, 1970, 11, 4269 - 4270.
14. As determined by filtration of the reaction mixture, washing with water, and determination of the pH of the aqueous phase.
15. The use of phosphorus pentoxide (1 equivalent to carboxylic acid) and t-butanol (5 equivalents to carboxylic acid) in chloroform, in the absence of anhydrous magnesium sulfate, afforded the desired t-butyl esters in yields comparable to those reported in the Table.
16. Altschul, R. J. Am. Chem. Soc., 1946, 68, 2605 - 2609.