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Synlett

Volumn , Issue 2, 2007, Pages 321-323

A novel NaI-promoted ring expansion of cyclopropylidene alcohols to dihydropyrans

(3) Fu, Weijun a Huang, Xian a,b Lin, Ying a

a ZHEJIANG UNIVERSITY (China)

b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY (China)

Author keywords

Cyclopropylidene alcohols; Dihydropyrans; Iodide anion; Ring expansion

Indexed keywords

ALCOHOL DERIVATIVE; CYCLOPROPYLIDENE ALCOHOL DERIVATIVE; DIHYDROPYRAN DERIVATIVE; PYRAN DERIVATIVE; SODIUM IODIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; SYNTHESIS;

EID: 33847072708 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-968016 Document Type: Article

Times cited : (7)

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- Typical Procedure for the Synthesis of Compound 3. A solution of 1a (160 mg, 1.0 mmol) with NaI (225 mg, 1.5 mmol) in 5 mL of MeCN-AcOH (10:1) was stirred at 80°C for 12 h. The mixture was then diluted with 10 mL of H2O and extracted three times with Et2O. The organic phases were combined and dried over MgSO4. After evaporation, the residues were purified via chromatography on silica gel with n-hexane-EtOAc as the eluent to afford 108 mg (67, of 3a as a liquid. IR (neat, 1652, 1600, 1448 cm-1. 1H NMR (400 MHz, CDCl3, δ, 7.25-7.34 (m, 5 H, 6.19-6.21 (m, 1 H, 4.50 (q, J, 2.8 Hz, 2 H, 3.85 (t, J, 5.6 Hz, 2 H, 2.30-2.34 (m, 2 H, 13C NMR (100 MHz, CDCl3, δ, 138.4, 136.1, 128.5, 127.3, 124.7, 121.2, 66.8, 64.0, 25.5. MS (70 eV, m/z, 160 36.26, M
- +].

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