Boron trifluoride mediated Prins reaction of methylene diacetate with styrenes. One-pot synthesis of 3-chloro-3-arylpropanols
SYNTHESIS-STUTTGART, sa.9, ss.1427-1432, 2006 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Basım Tarihi: 2006
- Doi Numarası: 10.1055/s-2006-926445
- Dergi Adı: SYNTHESIS-STUTTGART
- Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
- Sayfa Sayıları: ss.1427-1432
- Orta Doğu Teknik Üniversitesi Adresli: Evet
Özet
A one-pot procedure was developed for the synthesis of 3-chloro-3-arylpropanols, which are important starting materials for the synthesis of biologically active benzanilide derivatives. Styrenes were reacted with methylene diacetate in the presence of boron trifluoride to give the corresponding 3-chloro-3-arylpropanols in 36-84% yield by the Prins reaction. A strongly electron-donating methoxy substituent at either the ortho or para position of the styrene did not give the expected 3-chloro-3-arylpropanols due to polymerization. Styrene with a strongly electron-withdrawing nitro substituent gave the corresponding 3-chloro-3-arylpropanol in very low yield. Under the same reaction conditions, substituted norbornene gave a tricyclic ether. A very easy procedure for the synthesis of methylene diacetate is also reported.