Synthesis of β-hydroxy esters using highly active manganese

Tetrahedron Letters

Volumn 45, Issue 8, 2004, Pages 1807-1809

  Suh, YoungSung ^a   Rieke, Reuben D ^a  

^a UNIVERSITY OF NEBRASKA LINCOLN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ESTER DERIVATIVE; KETONE; LEWIS ACID; MANGANESE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; REACTION ANALYSIS; REFORMATSKY REACTION; STRUCTURE ANALYSIS; TEMPERATURE DEPENDENCE;

EID: 0842326650     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.11.045     Document Type: Article

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22. The following is a representative procedure: Ethyl α-bromoacetate (60 mmol) and benzaldehyde (58 mmol) were weighed separately. To the black slurry of active manganese in THF (30 mL) was added the mixture of benzaldehyde and ethyl α-bromoacetate drop by drop over 25 min. The addition was conducted at 0°C and the entire system was kept under argon. The reaction mixture was stirred at room temperature for about an hour after the addition was completed. The reaction was then quenched with 2 N hydrochloric acid (20 mL) or saturated ammonium chloride and the organic layer was separated from the acidic aqueous layer. The aqueous layer was extracted with ether (3 × 20 mL) and the combined organic phase was washed twice with saturated sodium hydrogen carbonate (10 mL) and water (10 mL). The ether extract was dried over anhydrous magnesium sulfate, filtered and the solvent was evaporated, resulting in a pale yellow liquid. The crude product was subjected to GLC, which showed no by-products. The crude product was purified by vacuum distillation or column chromatography yielding 90% of the corresponding compound.