A novelprocedurefor reductionandsimultaneousprotectionof phenolgroupsof hydroxycinnamicacidsto therelatedalcoholshas beendeveloped.Duringthe formationof mixedanhydridesfromtheacidsandan alkylchloroformate,thephenolwasprotectedas carbonate,andthe mixedanhydrideswerereducedwithan aqueoussolutionof sodiumborohydride.Freephenolswereobtainedby deprotectionundermildconditionswith30%aq.NH4OHin methanol.O-protectedphenolicalcoholscan be convertedby standardmethodsintoorthogonalprotectedderivatives.Thisrapidandefficientsyntheticmethodoffersa simpleandhigh-yieldpreparationoftheseimportantfinechemicals,overcomingthetediousandcostlyproceduresassociatewiththeuseof strongreducingagentssuchas LiAlH4andDIBALH.
A Facile Preparation of Hydroxycinnamyl Alcohols with Simultaneous Protection of Phenol Groups as Carbonate / Panzella, Lucia; DELLA GRECA, Marina; Longobardo, Luigi. - In: CHEMISTRYSELECT. - ISSN 2365-6549. - 3:38(2018), pp. 10637-10640. [10.1002/slct.201802099]
A Facile Preparation of Hydroxycinnamyl Alcohols with Simultaneous Protection of Phenol Groups as Carbonate
Lucia PanzellaMembro del Collaboration Group
;Marina Della GrecaMembro del Collaboration Group
;Luigi Longobardo
Writing – Original Draft Preparation
2018
Abstract
A novelprocedurefor reductionandsimultaneousprotectionof phenolgroupsof hydroxycinnamicacidsto therelatedalcoholshas beendeveloped.Duringthe formationof mixedanhydridesfromtheacidsandan alkylchloroformate,thephenolwasprotectedas carbonate,andthe mixedanhydrideswerereducedwithan aqueoussolutionof sodiumborohydride.Freephenolswereobtainedby deprotectionundermildconditionswith30%aq.NH4OHin methanol.O-protectedphenolicalcoholscan be convertedby standardmethodsintoorthogonalprotectedderivatives.Thisrapidandefficientsyntheticmethodoffersa simpleandhigh-yieldpreparationoftheseimportantfinechemicals,overcomingthetediousandcostlyproceduresassociatewiththeuseof strongreducingagentssuchas LiAlH4andDIBALH.| File | Dimensione | Formato | |
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