Never Underestimate The Influence Of (Tetrahydro-2H-pyran-4-yl)methyl 4-methylbenzenesulfonate

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In heterogeneous catalysis, the catalyst is in a different phase from the reactants. At least one of the reactants interacts with the solid surface in a physical process called adsorption in such a way. In an article, once mentioned the application of 101691-65-0, Name is (Tetrahydro-2H-pyran-4-yl)methyl 4-methylbenzenesulfonate,molecular formula is C13H18O4S, is a conventional compound. this article was the specific content is as follows.Application of 101691-65-0

GSK2981278A (1) is a RORgammainverse agonist used as a potential topical nonsteroidal therapy for psoriasis. New synthesis of 1 was developed based on a SNAr reaction of (tetrahydro-2H-pyran-4-yl)methanol with an aryl halide intermediate, prepared from 2-halobenzoic acids. The dianion underwent in situ N,O-bis-isobutylation, followed by a reduction to provide 1. The new route eliminated a genotoxic tosylate of (tetrahydro-2H-pyran-4-yl)methanol and a difficult reductive amination from the original synthesis starting from methyl salicylate. A primary version of the route has been scaled up to deliver 125 kg of 1. However, the heating of a strong base in DMSO for an extended period during the bis-alkylation was found to be a safety concern for manufacturing. A safer and greener process was then developed utilizing a facile N,O-bis-alkylation, which was conducted under phase transfer conditions with mild bases such as potassium carbonate and in green solvents such as water. The concise four stage sequence from 2-halobenzoic acids to GSK2981278A (1) had an overall yield of 41%.

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Reference:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics