1
720
M. J. Chae et al. / Tetrahedron Letters 52 (2011) 1718–1720
In summary, we have developed a new one-pot method for
3. Kim, M. S.; Choi, Y. M.; An, D. K. Tetrahedron Lett. 2007, 48, 5061; Song, J. I.; An, D.
K. Chem. Lett. 2007, 36, 886; Chae, M. J.; Song, J. I.; An, D. K. Bull. Korean Chem. Soc
007, 28, 2517.
transformation of esters to secondary alcohols, also involving allyl
alcohols, under mild reaction conditions without any isolation of
aldehyde intermediates. Accordingly, this methodology is believed
to be a useful alternative for direct preparation of secondary alco-
hols from common esters.
2
4.
Preparation of LDBBA. To a solution of t-butyl alcohol (5.16 mL, 55 mmol) in THF
(25 mL) was added n-butyllithium (20 mL, 2.5 M in hexane, 55 mmol) at 0 °C.
After being stirred for 1 h at room temperature, DIBALH (50 mL, 1.0 M in hexane,
50 mmol) was added dropwise to the reaction mixture at 0 °C and the mixture
was stirred for 2 h at room temperature to give a colorless homogeneous
solution. The LDBBA was most effective for partial reduction of esters when it
was solution in THF–hexane mixed solvent at 0 °C. The following experimental
procedure for the synthesis of 1-phenylpentan-1-ol is representative. To a solution
of ethyl benzoate (0.14 g, 1.0 mmol) in THF (10 mL) was slowly added LDBBA
(2.4 mL, 0.5 M in THF–hexane, 1.2 mmol) and the mixture was stirring for 3 h at
Acknowledgments
This work was supported by a National Research Foundation of
Korean grant funded by the Korean Government (2009-0066035).
We are also grateful for the support of Brain Korea 21.
0
°C. To this was slowly added n-butylmagnesium chloride (0.94 mL, 1.6 M in
Et O, 1.5 mmol). After being stirred for 30 min at room temperature, the
2
reaction mixture was quenched with aqueous 1 N HCl (10 mL) and extracted
with diethyl ether (2 Â 10 mL). The combined organic layers were dried over
4
MgSO and filtered. After the removal of solvents in vacuo, purification of the
References and notes
residue by column chromatography on silica gel gave 1-phenylpentan-1-ol
108 mg, 66%). All products in this Letter were confirmed by comparison with
(
1
.
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5
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