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Volumn , Issue 8, 2007, Pages 1317-1319

An efficient new procedure for the one-pot conversion of aldehydes into the corresponding nitriles

Author keywords

Aldehydes; DBU; Dehydration; Ethyl dichlorophosphate; Nitriles

Indexed keywords

ALDEHYDE DERIVATIVE; ALDOXIME; ETHYL DICHLOROPHOSPHATE; NITRILE; PHOSPHATE; UNCLASSIFIED DRUG;

EID: 34249793999     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-980338     Document Type: Article
Times cited : (40)

References (25)
  • 7
    • 85077888401 scopus 로고
    • For examples, see: a
    • For examples, see: (a) Sandnya, A. Synthesis 1982, 190.
    • (1982) Synthesis , pp. 190
    • Sandnya, A.1
  • 15
    • 0037281055 scopus 로고    scopus 로고
    • and references cited therein
    • (i) Sharghi, H.; Sarvari, M. H. Synthesis 2003, 243; and references cited therein.
    • (2003) Synthesis , pp. 243
    • Sharghi, H.1    Sarvari, M.H.2
  • 17
    • 34249784322 scopus 로고    scopus 로고
    • 2 and PhCH=NOH were obtained as the single stereoisomers. The stereochemistry remains to be determined.
    • 2 and PhCH=NOH were obtained as the single stereoisomers. The stereochemistry remains to be determined.
  • 18
    • 34249777887 scopus 로고    scopus 로고
    • An optimized amount of 3 Å MS was used. It was found that at least 120 mg of 3 Å MS was required for a quantitative conversion of 1.50 mmol of benzaldehyde (1) into benzonitrile 2
    • An optimized amount of 3 Å MS was used. It was found that at least 120 mg of 3 Å MS was required for a quantitative conversion of 1.50 mmol of benzaldehyde (1) into benzonitrile (2).
  • 19
    • 34249789091 scopus 로고    scopus 로고
    • Satisfactory spectral and LC-MS analytical data were obtained for all products; all known nitriles showed physical and spectral properties identical to those reported in the literature
    • Satisfactory spectral and LC-MS analytical data were obtained for all products; all known nitriles showed physical and spectral properties identical to those reported in the literature.
  • 20
    • 0033607627 scopus 로고    scopus 로고
    • For the preparation of compound 3, see: Falorni, M.; Giacomelli, G.; Porcheddu, A.; Teddei, M. J. Org. Chem. 1999, 64, 8962.
    • For the preparation of compound 3, see: Falorni, M.; Giacomelli, G.; Porcheddu, A.; Teddei, M. J. Org. Chem. 1999, 64, 8962.
  • 25
    • 34249786661 scopus 로고    scopus 로고
    • A representative experimental procedure is described for the preparation of benzonitrile (2, To a solution of benzaldehyde (1, 0.2 g, 1.88 mmol) in CH2Cl2 (8 mL, powdered 3 A MS (120 mg, 1.2 equiv of NH2OH·HCl (0.157 g. 2.26 mmol) and 5 equiv of DBU (143 g, 9.42 mmol) were successively added in one portion. The reaction mixture was stirred at r.t. for 10 h, cooled in an ice-water bath to 5°C, and 1.5 equiv of EtOPOCl2 (0.46 g, 2.83 mmol) were added. Then, stirring at r.t. was continued for an additional 5 h. The mixture was then quenched with aq NH4Cl2, extracted with CH2Cl2 and subjected to chromatographic purification on silica gel (15% EtOAc in hexane) to afford 2 in 96% yield (0.186 g, whose spectral data (IR, 1H NMR and 13C NMR) were identical to those of the authentic sample. Benzonitrile(2, IR KBr, 2228, 1701, 1597, 1583, 148
    • 25 -16.4 (c 0.98, dioxane)}.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.