Direct preparation of benzofurans from O-arylhydroxylamines

Synlett

Volumn , Issue 18, 2009, Pages 3003-3006

  Contiero, Fanny ^a   Jones, Kevin M ^a   Matts, Edward A ^a   Porzelle, Achim ^a   Tomkinson, Nicholas C O ^a  

^a CARDIFF UNIVERSITY   (United Kingdom)

Author keywords

Benzofuran; Hydroxylamine; Sigmatropic rearrangement

Indexed keywords

BENZOFURAN DERIVATIVE; HYDROXYLAMINE; KETONE;

ACYLATION; ARTICLE; ARYLATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS; SYNTHESIS;

EID: 72049097940     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1218273     Document Type: Article

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28. Typical Experimental Procedure; 1,2,3,4-Tetrahydrodibenzofuran (8):13 O-Phenylhydroxylamine hydrochloride (0.146 g, 1 mmol) was dissolved in THF (2mL) and warmed to 60 °C. After 5 min methanesulfonic acid (0.150 g, 2 mmol) and cyclohexanone (0.100 g, 1 mmol) were added and the reaction was monitored by TLC. On completion, the solvent was removed under reduced pressure. Purification by column chromatography (PE-EtOAc, 20:1) gave the title compound 8 (0.121 g, 70%) as a light yellow oil. 1H NMR (400 MHz, CDCl3): d = 7.28-7.32 (m, 2 H), 7.06-7.12 (m, 2 H), 2.62-2.66 (m, 2 H), 2.50-2.54 (m, 2 H), 1.80-1.86 (m, 2 H), 1.71-1.78 (m, 2 H). 13C NMR (62.5 MHz, CDCl3): d = 154.4, 154.0, 128.9, 123.0, 122.1, 118.4, 112.9, 110.8, 23.5, 23.0, 22.7, 20.5. LRMS (EI+): m/z = 172.1 [M]+. HRMS (MALDI): m/z [M]+ calcd for C12H12O: 172.0883; found: 172.0880.
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