Preparation of Methyl Ketones by the Sequential Treatment of Carboxylic Acids with Methyllithium and Chlorotrimethylsilane

Journal of Organic Chemistry

Volumn 48, Issue 9, 1983, Pages 1550-1552

  Rubottom, George M ^a   Kim, Chong Wan ^a  

^a UNIVERSITY OF IDAHO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001642794     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00157a038     Document Type: Article

References (13)

1. For a review on the reactions of carboxylic acids with organolithium reagents, see: Jorgenson, M. J. Org. React. (N.Y.) 1970, 18, 1.
2. House, H.O.; Bare, T.M. J. Org. Chem. 1968, 33, 943.
3. See, for instance: van Dorp, D.A.; Arens, J.F. Reel. Trav. Chim. Pays-Bas 1946, 65, 1607; and other references cited in ref 1.
4. House, H.O.; Bare, T.M. “Organic Syntheses”; Wiley: New York, 1973; Collect. Vol. V, p. 775. (b) Levine, R.; Harten, M.J.; Kadunce, W.M.J. Org. Chem. 1975, 40, 1770.
5. See, ref 1, p. 62, and: Anliker, R.; Miiller, M.; Perelman, M.; Wohlfahrt, J.; Heusser, H. Helv. Chim. Acta 1959, 42, 1071. (b) For an example of the use of DME as solvent, see ref 4a. (c) For an interesting case of the use of hexane as solvent, S66: Dalton, J.C.; Chan, H.-F. Tetrahedron Lett. 1973, 3145.
6. Danieli, N.; Mazur, Y.; Sondheimer, F. Tetrahedron 1966, 22, 3189. (b) Schneider, R.A.; Meinwald, J.J. Am. Chem. Soc. 1967, 89, 2023.
7. For the use of 3 equiv of methyllithium with a hydroxy acid, see: Billimoria, J.D.; Maclagan, N.F. J. Chem. Soc. 1951, 3067. (b) For the use of excess methyllithium, see: House, H.O.; Boots, S.G.; Jones, V.K.J. Org. Chem. 1965, 30, 2519. (c) Heathcock, C.H.; Kelly, T.R. Tetrahedron 1968, 24, 3753.
8. Vlad, P.F.; Kryshtal’, G.V.; Lazur'evskii, G.V. J. Gen. Chem. USSR (Engl. Transí.) 1967, 37, 2074. (b) Heusser, H.; Wohlfahrt, J.; Müller, M.; Anliker, R. Helv. Chim. Acta 1959, 42, 2140.
9. Nenitzescu, C.D.; Cioranescu, E. Chem. Ber. 1936, 69B, 1820.
10. The synthesis of this compound will be described elsewhere.
11. Dóring, C.-E.; Hauthal, H.G.; Noglik, H.; Prizkow, W. J. Prakt. Chem. 1964, 24, 183.
12. Detty, M.R.; Seidler, M.D. J. Org. Chem. 1981, 46, 1283.
13. Jakovac, I.J.; Jones, J.B. J. Org. Chem. 1979, 44, 2165.