CHEM01200604012 Dibakar Goswami - Homi Bhabha National ...

II.4 EXPERIMENTAL SECTION
Typical procedure for the In-and Ga-mediated allylation reaction in ionic liquids. A
mixture of In/Ga and allyl bromide in the RTIL (3 mL/mmol) was stirred at room
temperature for 0.5 h, followed by addition of the aldehyde. The reaction mixture was
stirred at room temperature till the completion of the reaction (cf. TLC). The mixture was
thoroughly extracted with Et 2 O (10 mL), the combined ether extracts evaporated in vacuo
and the residue purified by column chromatography (silica gel, EtOAc/hexane) to give the
respective products. Quantities of allyl bromide and the reaction times are specified in the
respective tables.
Following a similar method, allylation of 59a was also carried out in H 2 O and THF
using the amounts of the reagents as specified in the respective tables.
NMR experiments. A mixture of the In or Ga (1.0 mmol) and allyl bromide (1.0 mmol) in
the respective solvent (3 mL) was magnetically stirred at room temperature. Aliquots (35
μL) of reaction mixture were taken at different time intervals, and the 1 H NMR spectra
were recorded in CDCl 3 or D 2 O.
GLC experiments. A mixture of In (1.0 mmol) and allyl bromide (1.0 mmol) in
[bmim][Br] (3 mL) was magnetically stirred at room temperature. Aliquots (66 and 132
μL) of reaction mixture were drawn at different time intervals, extracted with Et 2 O (1 mL)
and the ether extract (1 μL) was analyzed by GLC (3% OV-17, 45 o C, isothermal).
1-Phenyl-but-3-en-1-ol 59a. Colourless liquid; IR: 3468, 922 cm -1 ; 1 H NMR: δ 1.94
(broad s, 1H), 2.45-2.56 (m, 2H), 4.74 (t, J = 6.8 Hz, 1H), 5.10-5.25 (m, 2H), 5.65-5.93 (m,
1H), 7.26-7.40 (m, 5H); 13 C NMR: δ 43.8, 73.2, 118.4, 125.8, 127.5, 128.4, 134.4, 143.8.
Anal. Calcd. for C 10 H 12 O: C, 81.06; H, 8.16%. Found: C, 81.26; H, 7.89%.
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