Esters ortho ester synthesis

Eliel, E. L. Nader, F. W. Conformational analysis. XX. The stereochemistry of reaction of Grignard reagents with ortho esters. Synthesis of 1,3-dioxanes with axial substituents at C-2.]. Am. Chem. Soc. 1970, 92, 584-590. 

DeWolfe, R. H. Synthesis of carboxylic and carbonic ortho esters. Synthesis 1974, 153-172. 

J. Heller, J. Barr, S.Y Ng, K. Schwach-Abdel-laoui and R. Gurny, Poly(ortho esters) synthesis, characterization, properties, and uses, Adv. Drug Deliv. Rev. 2002, 30, 1015-1039. 

Pinner Reaction (Amidine and Ortho Ester Synthesis)... 

Heller, J., Barr, J., Ng, S. Y., Abdellauoi, K. S. Gurny, R. 2002. Poly(ortho esters) synthesis, characterization, properties and uses. Advanced Drug Delivery Reviews, 54, 1015-1039. 

An alternative synthesis converts monohromopentaerythritol to the ortho ester, followed by reaction with cuprous acrylate. 

PINNER Imlno Ether Synthesis Synthesis of imlno ethers, amidines and ortho esters from nitnles. 

The synthesis and interconvereion of simple ortho esters has been reviewed R. H. DeWolfe, Synthesis, 153 (1974). 

Note that this method does not work on simple esters. In addition, TMSOCH2CH2OTMS/TMSOTF has been used to effect this conversion.The same process was used to introduce the cyclohexyl version of this ortho ester in a quassinoid synthesis. Its cleavage was effected with DDQ in aqueous acetone.(R,R)-2,3-Butanediol can be used to resolve the lactone. 

A salient structural feature of intermediate 18 (Scheme 2b), the retrosynthetic precursor of aldehyde 13, is its y,r5-unsaturated ester moiety. As it turns out, the Johnson ortho ester variant of the Clai-sen rearrangement is an excellent method for the synthesis of y,<5-unsaturated esters.11 In fact, the Claisen rearrangement, its many variants included, is particularly valuable in organic synthesis as a method for the stereocontrolled construction of trans di- and tri-substituted carbon-carbon double bonds.12,13 Thus, it is conceivable that intermediate 18 could be fashioned in one step from allylic alcohol 20 through a Johnson ortho ester Claisen rearrangement. In... 

Ortho esters, in synthesis of symmetrical trimethine thiazolocyanines, 54 Oxazolone, for neutrocyanines, 27 Oxidation potentials, of dyes, 75 of mesosubstituted dyes, in relation with absorption, 77 of polymethine dyes, 72 Oxidoreduction, relation between sensitizers, and silver halides, 78 4-Oxo-disubstituted 2-aminoselenazoles, table of products, 262 Oxonols, nomenclature of, 26 in synthesis of dimethine neutrocyanines, 62... 

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