A homologous enolate Truce-Smiles rearrangement

Tetrahedron Letters

Volumn 45, Issue 29, 2004, Pages 5669-5671

  Mitchell, Lorna H ^a   Barvian, Nicole C ^a  

^a PFIZER INC   (United States)

Author keywords

Rearrangement; Truce Smiles

Indexed keywords

2 HYDROXYACETOPHENONE; ACETOPHENONE DERIVATIVE; DIPHENYL ETHER DERIVATIVE; FLUORINE DERIVATIVE; KETONE; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; CHEMICAL REACTION; REACTION ANALYSIS;

EID: 3042582144     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.05.111     Document Type: Article

References (16)

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3. 4: C, 65.37; H, 4.31; N, 5.44%. Found: C, 65.14; H, 4.07; N, 5.34%
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15. 4: C, 65.37; H, 4.31; N, 5.44%. Found: C, 65.11; H, 4.09; N, 5.39%
16. All products analyzed correctly by microanalysis. Representative procedure: A mixture of 4-fluoronitrobenzene (0.5 mL, 4.7 mmol), 2′-hydroxyacetophenone (0.96 g, 7.1 mmol), and potassium carbonate (2.0 g, 14.0 mmol) in DMF (20 mL) was heated with stirring at 120°C for 2 h. The reaction mixture was poured into an ice water mixture and the resulting tan solid was collected by filtration and dried. The solid was triturated with ether/hexane to cleanly give 3 as a cream colored solid, 0.89 g (73%)