38222-83-2 Usage
Description
2,6-Di-tert-butyl-4-methylpyridine is a sterically hindered, non-nucleophilic base that can differentiate between protonic and Lewis acids. It is a light yellow powder and is known for its ability to facilitate the high-yield conversion of aldehydes and ketones to vinyl triflates. 2,6-Di-tert-butyl-4-methylpyridine also inhibits desilylation and hydration of the products during GaCl3-catalyzed ortho-ethynylation of phenol.
Uses
Used in Organic Synthesis:
2,6-Di-tert-butyl-4-methylpyridine is used as a base for the generation of enol triflates from ketones using trifluoromethanesulfonic anhydride. This application is particularly useful in the synthesis of various organic compounds.
Used in the Synthesis of 1,2-Dihydro-2-Silanaphthalene Derivatives:
In this application, 2,6-Di-tert-butyl-4-methylpyridine is used as a base in the synthesis of 1,2-dihydro-2-silanaphthalene derivatives, which are important intermediates in the development of novel materials and pharmaceuticals.
Used in PtCl4-Catalyzed Cyclization Reactions of Homopropargyl Azide Derivatives:
2,6-Di-tert-butyl-4-methylpyridine serves as a base in PtCl4-catalyzed cyclization reactions of homopropargyl azide derivatives, which is a crucial step in the synthesis of complex organic molecules.
Used in the Diastereoselective Synthesis of β-Thiomannopyranosides:
2,6-Di-tert-butyl-4-methylpyridine is also utilized as a base in the diastereoselective synthesis of β-thiomannopyranosides, which are significant in the field of carbohydrate chemistry and have potential applications in drug development and material science.
Synthesis Reference(s)
The Journal of Organic Chemistry, 41, p. 3034, 1976 DOI: 10.1021/jo00880a027
Purification Methods
A possible impurity is 2,6-di-tert-butyl-4-neopentylpyridine. Attempts to remove coloured impurities directly by distillation, acid-base extraction or treatment with activated charcoal were unsuccessful. Pure material is obtained by dissolving 0.3mole of the alkylpyridine in pentane (150mL) and introducing it at the top of a cold water jacketed chromatographic column (40 x 4.5cm) (cooling is necessary because the base in pentane reacts exothermically with alumina) containing activated and acidic alumina (300g). The column is eluted with pentane using a 1L constant pressure funnel fitted at the top of the column to provide slight pressure. All the pyridine is obtained in the first two litres of eluent (the progress of elution is monitored by spotting a fluorescent TLC plate and examining under short wave UV light—a dark blue spot is evidence for the presence of the alkylpyridine). Elution is complete in 1hour. Pentane is removed on a rotovap with 90-93% recovery yielding a liquid which solidifies on cooling, m 31-32o, and the base can be distilled. The HPtCl6 salt has m 213-314o(dec), and the CF3SO3H salt has m 202.5-203.5o (from CH2Cl2). [Anderson & Stang Org Synth Coll Vol VII 144 1981, Beilstein 20/6 V 190.]
Check Digit Verification of cas no
The CAS Registry Mumber 38222-83-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,8,2,2 and 2 respectively; the second part has 2 digits, 8 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 38222-83:
(7*3)+(6*8)+(5*2)+(4*2)+(3*2)+(2*8)+(1*3)=112
112 % 10 = 2
So 38222-83-2 is a valid CAS Registry Number.
InChI:InChI=1/C14H23N/c1-10-8-11(13(2,3)4)15-12(9-10)14(5,6)7/h8-9H,1-7H3
38222-83-2Relevant articles and documents
Palladium-Catalyzed Methylation of Aryl, Heteroaryl, and Vinyl Boronate Esters
Haydl, Alexander M.,Hartwig, John F.
supporting information, p. 1337 - 1341 (2019/02/26)
A method for the direct methylation of aryl, heteroaryl, and vinyl boronate esters is reported, involving the reaction of iodomethane with aryl-, heteroaryl-, and vinylboronate esters catalyzed by palladium and PtBu2Me. This transformation occurs with a remarkably broad scope and is suitable for late-stage derivatization of biologically active compounds via the boronate esters. The unique capabilities of this method are demonstrated by combining carbon-boron bond-forming reactions with palladium-catalyzed methylation in a tandem transformation.
Diacylation of alkenes catalyzed by sulfonic acids 3: application of weak sulfonic acids to the regioselective synthesis of pyrylium salts from isoolefins and linear olefins
Rajoharison, Harivelo G.,Roussel, Christian
, p. 307 - 313 (2007/10/02)
The use of weak sulfonic acids (methanesulfonic and α-carboxyalkanesulfonic acids) as catalysts in diacylation of disymmetrical isoalkenes by carboxylic acid anhydrides afford almost exclusively the more substituted pyrylium salt.Particularly, simple isoalkenes (generated in situ from dimethyl alkyl carbinols) and citronellol lead 2,3,4,6-tetrasubstituted pyrylium salts in high yields.Diacylation of 1-alkenes lead to 2,3,6-trialkyl-substituted pyrylium without isomerization but in low yield.The observed lower regioselectivities in comparative reactions catalyzed by strong protonic acids (perchloric acid or trifluoromethanesulfonic acid which are the classical catalysts in this kind of synthesis) confirm that the strenght of the catalyst governs the regioselectivity of the diacylation of olefins when carboxylic acid anhydrides are used as sources of acylating agents.In all cases, the obtained pyrylium salts were transformed into the corresponding pyridines by treatment with concentrated ammonia.
Reactions of Dianions with Nitriles. A New Pyridine Synthesis
Bates, Robert B.,Gordon, Bernard,Keller, Philip C.,Rund, John V.,Mills, Nancy S.,
, p. 168 - 169 (2007/10/02)
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