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Volumn 39, Issue 3, 2010, Pages 246-247

A rapid and efficient synthesis of allyl iodides from Baylis-Hillman adducts: A facile synthesis of semiplenamide D

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EID: 77249103999 PISSN: 03667022 EISSN: 13480715 Source Type: Journal
DOI: 10.1246/cl.2010.246 Document Type: Article

Times cited : (5)

References (23)

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- General experimental procedure: To a solution of BaylisHillman adduct (0.5mmol) and Et3SiH (0.5mmol) in CHCl3 (5 mL, iodine (0.5mmol) was added. The mixture was stirred for 5min when the reaction was complete. The solution was removed under vacuum and water (10 mL) was added to the residue. The mixture was extracted with EtOAc (3 x 10 mL) and the extract was dried and concentrated. The crude mass was subjected to column chromatography (silica gel, hexane-EtOAc) to obtain pure allyl iodide. The spectral and analytical data of some representative compounds are given below. 2d: 1HNMR (200 MHz, CDCl3, δ 6.88 (1H, t, J, 7.0 Hz, 4.12 (2H, s, 3.80 (3H, s, 2.252.19 (2H, s, 1.16 (3H, t, J, 7.0 Hz, 13CNMR 50 MHz, CDCl3, δ 165.8, 142.2, 129.9, 52.0, 29.6, 21.8, 12.1; ESIMS: m/z 255 [M, H, 127 [M, I, Calcd for C7H11IO2: C, 33.08; H
- +; Found: m/z 446.3628.

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