Skip to main content
SpringerLink
Log in

Reaction of furfural and its diethylacetal with alkyl diazoacetates and dimethyl diazomalonate in the presence of boron trifluoride etherate or rhodium acetate

  • Published:
Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    The reaction of alkyl diazoacetates (ADA) with furfural in the presence of Et2O·BF3 at 20°C leads mainly to the product of the formal implantation of the alkoxycarbonylmethylene fragment into the aldehyde C-H bond, while in the same reaction in the presence of (Rh(OAc)2, a mixture of isomeric 2,5-di (2-furyl)-4-alkoxycarbonyl-1,3-dioxalanes is formed in a 60% overall yield.

  2. 2.

    The reaction of furfural diethylacetal with ADA in the presence of Et2O·BF3 at 20°C gave yields of up to 60% of 1-(2-furyl)-1-alkoxycarbonyl-2,2-diethoxyethanes that C1-C2are products of the formal implantation of the alkoxycarbonylmethylene fragment into the C1-C2 bond. However, in the presence of Rh(OAc)2 in the same reaction, the alkyl esters of 3-diethoxy-methyl-2-oxabicyclo[3.1.0]-3-hexene-6-carboxylic and 6,6-diethoxy-1,3-hexadien-5-one-1-carboxylic acid are formed in 60–70% overall yields.

  3. 3.

    The reaction of furfural diethylacetal with dimethyl diazomalonate catalyzed by Rh(OAc)2 at 20°C leads to the dimethyl ester of Z-6,6-diethoxy-1,3-hexadien-5-one-1,1-di-carboxylic acid in a 63% yield.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

Literature cited

  1. M. P. Doyle, M. L. Trudell, and J. W. Terpstra, J. Org. Chem.,48, 5146 (1983).

    Google Scholar 

  2. M. P. Doyle, J. H. Griffin, M. S. Chinn, and D. van Leusen, J. Org. Chem.,49, 1917 (1984).

    Google Scholar 

  3. O. M. Nefedov, L. E. Saltykova, A. E. Vasil'vitskii, and V. M. Shostakovskii, Izv. Akad. Nauk SSSR, Ser. Khim., 2153 (1986).

  4. W. L. Mock and M. E. Hartman, J. Org. Chem.,42, 459 (1977).

    Google Scholar 

  5. J. Noichi, Nippon Kagaku Zasshi,88, 565 (1967); Chem. Abstr.,69, 10389x (1968).

    Google Scholar 

  6. L. Claisen, Chem. Ber.,40, 3903 (1907).

    Google Scholar 

  7. L. Gatterman and H. Wiegand, Practical Course in Organic Chemistry [Russian translation], Goskhimizdat, Moscow (1948), p. 310.

    Google Scholar 

  8. R. Ciganek, J. Org. Chem.,30, 4366 (1965).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow

    L. E. Saltykova, A. E. Vasil'vitskii, V. M. Shostakovskii & O. M. Nefedov

Authors
  1. L. E. Saltykova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. E. Vasil'vitskii
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. V. M. Shostakovskii
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. O. M. Nefedov
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 4, pp. 342–847, April, 1988.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Saltykova, L.E., Vasil'vitskii, A.E., Shostakovskii, V.M. et al. Reaction of furfural and its diethylacetal with alkyl diazoacetates and dimethyl diazomalonate in the presence of boron trifluoride etherate or rhodium acetate. Russ Chem Bull 37, 722–727 (1988). https://doi.org/10.1007/BF01455486

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF01455486

Keywords

Search

Navigation