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Volumn 5, Issue 7, 2008, Pages 527-529

Facile and efficient synthesis of ethyl 3-Oxo-5-arylthiopentanoates, the precursors for nazarov reagent

Author keywords

Keto ester; Blaise reaction; Nazarov reagent

Indexed keywords

EID: 57349200375 PISSN: 15701786 EISSN: None Source Type: Journal
DOI: 10.2174/157017808785982121 Document Type: Article

Times cited : (12)

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24
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- Representative procedure for the conversion of nitriles 5 to β-keto esters 6: Ethyl 3-oxo-5-phenylthiopentanoate 6a: To the stirred suspension of zinc 4.0 g (zinc dust, <10 micron, 61.3 mmol) in THF (25 mL) TMSCI (100 mg, 3 mol, was added at rt. The mixture was refluxed for 15 min and the nitrile 5a (5 g, 30.6 mmol, ethyl bromoacetate 10.25 g (61.3 mmol) were added drop wise, at this temperature, simultaneously over 30 min with two pressure equalizers. The reaction was allowed to continue for 4 h while monitoring it by GC-MS. After completion of the reaction, the mixture was cooled to 0-5 °C and aq 3 N HCI (20 mL) was added drop wise. The resulting mixture was extracted with diethyl ether (2 × 25 mL, The separated organic layer was washed with cold water (50 mL, brine (15 mL, dried (anhydrous Na2SO4) and concentrated. The residue on silica gel (100-200 mesh) column chromatographic purification with increasing amounts of
- 3) 200.1, 166.5, 129.5, 128.9, 126.2, 96.1, 61.1, 49.1, 42.4, 27.1, 14.1 ppm.

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