Efficient synthesis of 3-oxygenated benzothiophene derivatives

Tetrahedron Letters

Volumn 48, Issue 13, 2007, Pages 2349-2352

  Zhang, Fuyao ^a   Mitchell, David ^a   Pollock, Patrick ^a   Zhang, Tony Y ^a  

^a ELI LILLY AND COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 BROMO 3 OXYBENZOTHIOPHENE DERIVATIVE; BENZOTHIOPHENE DERIVATIVE; PHENOL DERIVATIVE; SELECTIVE ESTROGEN RECEPTOR MODULATOR; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; ELIMINATION REACTION; OXYGENATION; REACTION ANALYSIS; SYNTHESIS;

EID: 33847307782     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.01.141     Document Type: Article

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23. 3) δ 162.9, 161.9, 157.5, 147.5, 141.8, 122.8, 121.7, 121.3, 118.7, 115.9, 106.7, 101.4, 66.7, 58.1, 56.3, 55.3, 26.1, 24.4. Preparation of 13: To a solution of sulfone 12 (10.5 g, 25.3 mmol) in 100 mL of THF was added a solution of DIBAL (100 mL, 1.0 M, 100 mmol) in methylene chloride at ambient temperature. The resulting solution was heated at 50 °C for 18 h. Additional 50 mL of DIBAL was added and continued to stir at 50 °C for additional 6 h. The reaction was quenched by the addition of saturated sodium sulfate. White solids were removed by filtration. The filtrate was washed with water and brine, and dried over sodium sulfate.