Methoxymethyl ethers
MOM-OR, MOM ether
T. W. Green, P. G. M. Wuts, Protective Groups in Organic Synthesis, Wiley-Interscience, New York, 1999, 27-33, 708-711.
Stability
| H2O: | pH < 1, 100°C | pH = 1, RT | pH = 4, RT | pH = 9, RT | pH = 12, RT | pH > 12, 100°C |
| Bases: | LDA | NEt3, Py | t-BuOK | Others: | DCC | SOCl2 |
| Nucleophiles: | RLi | RMgX | RCuLi | Enolates | NH3, RNH2 | NaOCH3 |
| Electrophiles: | RCOCl | RCHO | CH3I | Others: | :CCl2 | Bu3SnH |
| Reduction: | H2 / Ni | H2 / Rh | Zn / HCl | Na / NH3 | LiAlH4 | NaBH4 |
| Oxidation: | KMnO4 | OsO4 | CrO3 / Py | RCOOOH | I2, Br2, Cl2 | MnO2 / CH2Cl2 |
0.01 mol-% Zinc(II) salts catalyze the reaction between acetals and acid halides
to provide haloalkyl ethers in near-quantitative yield in 1 - 4 h. The solutions
of haloalkyl ethers can be utilized directly in reactions in which the presence
of the ester byproduct does not interfere. Excess carcinogenic haloalkyl ether
is destroyed on workup.
M. A. Berliner, K. Belecki, J. Org. Chem., 2005,
70, 9618-9621.
Different types of unsymmetrically protected diols are available from the
methylene acetal in a one-pot procedure. Monoprotected 1,2-diols with a silyl
group at the less hindered hydroxy group as well as with a MOM group at the more
hindered can be isolated in good yields. The reaction conditions are mild
without affecting other functional groups.
H. Fujioka, K. Senami, O. Kubo, K. Yahata, Y. Minamitsuji, T. Maegawa, Org. Lett., 2009,
11, 5138-5141.
A simple and efficient method has been developed for chemoselective deprotection
of phenolic methoxymethyl (MOM) ethers at room temperature using
silica-supported sodium hydrogen sulfate as a heterogeneous catalyst.
C. Ramesh, N. Ravindranath, B. Das, J. Org. Chem., 2003,
68, 7101-7103.
Red-Al is an efficient chelation-controlled reducing reagent for acyclic
acetal-protected R-hydroxy ketones. Typically, high diastereomeric ratios
and yields can be achieved for the synthesis of 1,2-anti-diols.
N. Bajwa, M. P. Jennings, J. Org. Chem., 2008,
73, 3638-3641.
