1116
J. M. Khurana et al.
stirrer and 0.2 g 1a (1.11 mmol) dissolved in 10 cm3 of
methanol was placed in it. NiCl2Á6H2O (2.1 g, 8.88 mmol)
was added followed by 0.33 g NaBH4 (8.88 mmol) cau-
tiously. The reaction mixture was stirred vigorously at
room temperature. The progress of the reaction was
monitored by TLC using ethyl acetate:petroleum ether
(5:95) as eluent. TLC showed complete disappearance of
the starting material after 2 h. The reaction was quenched
by adding 10 cm3 of methanol. The reaction mixture was
filtered through a Celite pad (*2.5 cm) and washed with
methanol (2 9 10 cm3). Water (20 cm3) was added to the
filtrate, which was extracted with ethyl acetate
(3 9 10 cm3). The combined extract was dried over anhyd.
MgSO4. After concentration, followed by column chro-
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matography
on
neutral
alumina
using
ethyl
acetate:petroleum ether (3:97, v/v) as eluent, acetophenone
was obtained in 82 % yield as characterized by superim-
1
posable IR spectra and H NMR spectra.
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General procedure: reduction of 2-methyl-2-phenyl-1,3-
oxathiolane (1a)
In a typical reaction, a 50 cm3 round-bottomed flask fitted
with a reflux condenser was mounted over a magnetic
stirrer and 0.2 g, 1a (1.11 mmol) dissolved in 10 cm3 of
methanol was placed in it. NiCl2Á6H2O (1.58 g,
6.66 mmol) was added followed by 0.71 g NaBH4
(18.78 mmol) cautiously. The reaction mixture was stirred
vigorously at room temperature. The progress of the
reaction was monitored by TLC using ethyl acetate:pe-
troleum ether (5:95) as eluent. TLC showed complete
disappearance of the starting material after 2.5 h. The
reaction was quenched by adding 10 cm3 of methanol. The
reaction mixture was filtered through a Celite pad
(*2.5 cm) and washed with methanol (2 9 10 cm3).
Water (20 cm3) was added to the filtrate, which was
extracted with ethyl acetate (3 9 10 cm3). The combined
extract was dried over anhyd. MgSO4, decanted through a
cotton pad, and concentrated on a rotary evaporator to
obtain 0.12 g of 1-phenylethanol (87 %) as characterized
1
by superimposable IR spectra and H NMR spectra.
Acknowledgments Financial assistance for the project by UGC
[Project No. F-32-203/2006(SR)] and JRF, SRF to DM and KD by
CSIR is gratefully acknowledged.
38. Beilstein F (1899) Handbuch der Organischen Chemie, vol 4, 3rd
edn. Leopold Voss, Hamburg, p 1
39. Buckingham J (ed) (1982) Dictionary of organic compounds, 5th
edn. Chapman and Hall, New York
References
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synthesis, 3rd edn. Wiley, New York
123