4-(Dimethylamino)pyridine is a useful nucleophilic catalyst for various reactions viz. esterifications with anhydrides, the Baylis-Hillman reaction, hydrosilylations, tritylation and Steglich rearrangement. It is also an effective catalyst for transesterification of beta-keto esters and silylation of alcohols.
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Applications
4-(Dimethylamino)pyridine is a useful nucleophilic catalyst for various reactions viz. esterifications with anhydrides, the Baylis-Hillman reaction, hydrosilylations, tritylation and Steglich rearrangement. It is also an effective catalyst for transesterification of beta-keto esters and silylation of alcohols.
Solubility
Soluble in methanol, benzene, ethyl acetate, chloroform, methylene chloride, acetone, and acetic acid. Slightly soluble in ether, diisopropyl ether, cyclohexane, hexane, and water.
Notes
Incompatible with strong oxidizing agents and strong acids.
RUO – Research Use Only
General References:
- Hypernucleophilic catalyst. Greatly accelerates the acylation of hindered, including tertiary, alcohols; reviews: Angew. Chem. Int. Ed., 17, 569 (1978). Chem. Soc. Rev., 12, 129 (1983). Catalyst for acylation of alcohols using mixed anhydrides of hindered carboxylic acids with methanesulfonic acid: Synth. Commun., 12, 727 (1982), and with mixed carboxylic anhydrides: J. Org. Chem., 50, 560 (1985). In the Yamaguchi method of macrocyclic lactonization the mixed anhydride formed with 2,4,6-Trichlorobenzoyl chloride, L14159 is cyclized with 2 equiv. of DMAP; high dilution conditions are not required: Bull. Chem. Soc. Jpn., 52, 1989 (1979). For improved method in a high yield synthesis of erythronolide A, see: J. Org. Chem., 55, 7 (1990).
- Greatly increases the rate of ester and thio ester formation in the carbodiimide method of coupling (Steglich esterification): Angew. Chem. Int. Ed., 17, 522 (1978). For similar use in macrolactonizations, see: J. Org. Chem., 50, 2394 (1985), and in carbodiimide peptide coupling reactions: Int. J. Pept. Prot. Res., 18, 459 (1981). For peptide reagents, see Appendix 6.
- Effective catalyst for transesterification of ß-keto esters in toluene: J. Org. Chem., 50, 3618 (1985), and for smooth decarboalkoxylation of enolizable ß-keto esters in toluene containing a small amount of water: J. Org. Chem., 54, 3474 (1989). Under these conditions, other bases (N,N-dimethylaniline, pyridine, tetra-n-pentylammonium bromide) are ineffective.