91970-13-7Relevant academic research and scientific papers
Methoxymethylation of substituted alcohols using dimethoxymethane over Mo(VI)/ZrO2
Shyamsundar,Mohamed Shamshuddin,Ananda,Pratap
, p. 655 - 660 (2018/02/09)
The methoxymethylation reaction of alcohols was studied on Mo/ZrO2 (MZ) catalysts. The catalyst containing 5, 10 and 15 % Mo(VI) ions was prepared by solution combustion method. These solid acid catalytic materials were characterized by NH3- TPD, powder XRD, BET, FTIR spectroscopy, scanning electron microscopy, transmission electron spectroscopy and ICP- OES techniques. These catalysts were evaluated for their catalytic activity in the synthesis of methoxymethylation reactions of various substituted alcohols with dimethoxymethane in shorter reaction times (20 min) at moderate temperature (40 °C) with excellent yields (around 99 %). The main features of the Mo/ZrO2 catalyzed reaction are high yields, ease of scale up to gram scale, recyclable catalysts, inexpensive reagents, ecofriendly catalysts and a solvent free approach for the synthesis of methoxymethylated products.
A non-heme iron(III) complex with porphyrin-like properties that catalyzes asymmetric epoxidation
Niwa, Takashi,Nakada, Masahisa
supporting information; experimental part, p. 13538 - 13541 (2012/10/08)
In this report, we describe an iron(III) complex containing a carbazole-based tridentate ligand that catalyzes highly enantioselective asymmetric epoxidation of (E)-alkenes at room temperature. The non-heme iron(III) complex has a five-coordinated trigonal-bipyramidal structure, and its two-electron oxidized state has the similar electronic structure as that of iron porphyrins.
H3PW12O40at the[bmim][FeCl4]: A green catalytic system for alkoxymethylation of alcohols and their one-pot interconversion to acetates and TMS-ethers
Mohammadpoor-Baltork,Moghadam,Tangestaninejad,Mirkhani,Khosropour,Mirjafari
experimental part, p. 513 - 524 (2012/06/16)
12-Tungstophosphoric acid immobilized on [bmim][FeCl4] was found to be an efficient catalyst for chemoselective methoxymethylation and ethxoymethylation of alcohols and also one-pot conversion of MOM- or EOM-ethers to their corresponding acetates and TMS-ethers under thermal conditions and microwave irradiation. These procedures were simple, rapid and the corresponding products were obtained in high yields. The catalyst exhibited remarkable reactivity and was reusable.
[InCl4]: An efficient catalyst-medium for alkoxymethylation of alcohols and their interconversion to acetates and TMS-ethers
Mohammadpoor-Baltork, Iraj,Moghadam, Majid,Tangestaninejad, Shahram,Mirkhani, Valiollah,Khosropour, Ahmad Reza,Mirjafari, Arsalan
experimental part, p. 568 - 579 (2012/05/05)
A simple, green and chemoselective method for methoxymethylation and ethoxymethylation of primary and secondary alcohols using a Lewis acidic room temperature ionic liquid, [C4mim][InCl4], as catalyst and reaction medium under ambient temperature, microwave and ultrasonic irradiations is reported. In this catalytic system, the corresponding MOM-and EOM-ethers are obtained in excellent yields and in short reaction times. Furthermore, this catalytic system was used for mild and efficient transformations of these protected alcohols to their corresponding acetates and trimethylsilyl ethers under thermal conditions and microwave and ultrasonic irradiations.
The reaction of acetal-type protective groups in combination with TMSOTf and 2,2′-bipyridyl; Mild and chemoselective deprotection and direct conversion to other protective groups
Fujioka, Hiromichi,Minamitsuji, Yutaka,Kubo, Ozora,Senami, Kento,Maegawa, Tomohiro
experimental part, p. 2949 - 2960 (2011/05/12)
A mild and chemoselective deprotection method of various acetal-type protective groups, such as MOM, MEM, BOM, and SEM ethers, has been developed. The combination of TMSOTf and 2,2′-bipyridyl was very effective for the deprotection, and the reaction proceeded via the formation of pyridinium intermediates, which were hydrolyzed to the corresponding alcohols in good to high yields. The features of this method are mild (almost neutral) reaction conditions and the tolerability of acid-sensitive functional groups. This method is also applicable for the direct conversion of MOM ether to BOM or SEM ether using the appropriate alcohols instead of H2O.
High-valent [SnIV(Br8TPP)(OTf)2] as a highly efficient and reusable catalyst for selective methoxymethylation of alcohols and phenols: The effect of substituted bromines on the catalytic activity
Moghadam, Majid,Tangestaninejad, Shahram,Mirkhani, Valiollah,Mohammadpoor-Baltork, Iraj,Khajehzadeh, Mostafa,Kosari, Farshid,Araghi, Mehdi
experimental part, p. 238 - 243 (2010/04/04)
High-valent tin(IV)octabromotetraphenylporphyrinato trifluoromethanesulfonate, [SnIV(Br8TPP)(OTf)2], was used for selective methoxymethylation of alcohols and phenols with formaldehyde dimethyl acetal (FDMA) at room temper
Remarkable effect of 2,2′-bipyridyl: Mild and highly chemoselective deprotection of methoxymethyl (MOM) ethers in combination with TMSOTf (TESOTf)-2,2′-bipyridyl
Fujioka, Hiromichi,Kubo, Ozora,Senami, Kento,Minamitsuji, Yutaka,Maegawa, Tomohiro
supporting information; experimental part, p. 4429 - 4431 (2009/12/29)
The remarkable effect of 2,2′-bipyridyl led to the successful development of the mild and highly chemoselective deprotection method of methoxymethyl (MOM) ethers using the combination of TMSOTf (or TESOTf) and 2,2′-bipyridyl; this method can be applied to the direct conversion of the MOM group to other ethereal protective groups (e.g. benzyloxymethyl) with the corresponding alcohols. The Royal Society of Chemistry 2009.
H3PW12O40 - A selective, environmentally benign, and reusable catalyst for the preparation of methoxymethyl and ethoxymethyl ethers and their deprotections under mild conditions
Mohammadpoor-Baltork, Iraj,Moghadam, Majid,Tangestaninejad, Shahram,Mirkhani, Valiollah,Mirjafari, Arsalan
, p. 831 - 840 (2008/12/21)
Different types of primary and secondary alcohols were efficiently transformed to their corresponding methoxymethyl (MOM) and ethoxymethyl (EOM) ethers in the presence of catalytic amounts of H3PW 12O40 at room temperature under solvent-free conditions. Selective protection of primary and secondary alcohols in the presence of phenols and tertiary alcohols was achieved by this method. Deprotection of these ethers to their parent alcohols was also performed using this catalyst in ethanol under reflux conditions. We have also found that primary and secondary MOM- and EOM-ethers are selectively deprotected in the presence of phenolic and tertiary ones, methyl and benzyl ethers, esters, and trimethylsilyl ethers by this catalyst. The notable advantages of this protocol are high yields, short reaction times, easy work-up, non-toxicity, easy availability and handling, eco-friendly, and reusability of the catalyst.
Molybdatophosphoric acid as a catalyst for the methoxymethylation of alcohols under solvent-free conditions
Zolfigol, Mohammad Ali,Shiri, Morteza
, p. 165 - 166 (2007/10/03)
The methoxymethylation of alcohols was performed using formaldehyde dimethoxy acetal in the presence of H3PMo12O 40·xH2O at room temperature under solvent-free conditions.
Methoxymethylation of alcohols, phenols, and avermectin aglycones using MOM-2-pyridylsulfide
Marcune,Karady,Dolling,Novak
, p. 2446 - 2449 (2007/10/03)
Methoxymethyl-2-pyridylsulfide (MOM-ON) is an effective methoxymethylating reagent when used in conjunction with AgOTf, NaOAc, and THF. A wide range of MOM ethers are produced from corresponding phenols and alcohols, including tertiary and allylic alcohols, in good yields and under mild, neutral conditions. This method is also effective for the methoxymethylation of avermectin aglycones.
