10.1002/ejoc.201801438
European Journal of Organic Chemistry
FULL PAPER
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hexane gradient to give 116 mg (72%) of 4a as a yellow oil: Rf = 0.19
(hexane:EtOAc,, 5:1).
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5.2. The suspension of Mg (73 mg, 3 mmol), CH2Cl2 (5 mL), Toluene (1.5
ml) and TiCl4 (4 mL, 1 M in CH2Cl2, 4 mmol) was stirred for 1 min at -20
oC, then added a solution of 1i ( 112 mg, 1 mmol) and 1s ( 170 mg, 1 mmol)
in CH2Cl2 (1 mL). After being stirred for 5 min, THF (1.5 mL) was added.
°
The black-brown slurry was stirred for 1 h at -20 C and then saturated
potassium carbonate solution (10 mL) and dichloromethane (20 mL) were
added and stirred until the phases were separated. The organic layer was
dried (MgSO4), filtered, and concentrated in vacuum. The product was
purified by flash chromatography on silica gel with a 10-30% EtOAc:
hexane gradient to give 134 mg (83%) of 4i as a yellow oil: Rf = 0.22
(hexane:EtOAc, 5:1).
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We thank the National Science Council of the Republic of China
for generous financial support.
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Keywords: Halomethyl carbinol • Titanium • Synthetic methods •
Chemoselectivity • Carbonyl compounds
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