Indium mediated allylation of β-chloro-/β-alkoxy vinylaldehyde: A facile one pot synthesis of 1-chloro-/1-alkoxy hexa-1,5-diene-3-ol derivatives

Synthetic Communications

Volumn 33, Issue 1, 2003, Pages 1-9

  Pan, Dipanjan ^a   Kar, Gandhi K ^a   Ray, Jayanta K ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

1 CHLOROHEXA 1,5 DIEN 3 OL; 2 CHLOROVINYL ALDEHYDE DERIVATIVE; ALDEHYDE; ALKADIENE; UNCLASSIFIED DRUG;

ALLYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHIRALITY; DATA ANALYSIS; DERIVATIZATION; DRUG ISOLATION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0037278740     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120015553     Document Type: Article

References (31)

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28. Typical experimental procedure: A mixture of β-chlorovinylaldehyde (1 mmol), allyl bromide (3 mmol), indium metal (Sisco Research Laboratory, India) (2 mmol), sodium iodide (3 mmol) in dimethyl formamide (4-5 mL) was stirred at 25°C until completion of the reaction (checked by TLC). The reaction mixture was quenched with a few drops of 1NHCl, diluted with water and extracted with diethyl ether. After usual work up, the crude product obtained was purified by column chromatography (silica gel).
29. All compounds gave satisfactory elemental and spectroscopic data;
30. 13CNMR 40.81, 68.88, 109.90, 118.58, 118.73, 128.13, 128.69, 133.51. CHN calcd: C (66.82), H (5.57). Observed: C (66.57), H (5.31).
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