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2-Methoxypropene is an ether with the chemical formula C 4 H 8 O. It is a reagent used in organic synthesis to introduce a protecting group for alcohols, [1] and the conversion diols to the acetonide group. [3] 2-Methoxypropene can be prepared by the elimination of methanol from dimethoxypropane, [4] or by the addition of methanol to propyne or ...
With acetone or 2,2-dimethoxypropane as the acetalisation reagent the reaction is under thermodynamic reaction control and results in the pentose 2. The latter reagent in itself is an acetal and therefore the reaction is actually a cross-acetalisation. Kinetic reaction control results from 2-methoxypropene as the reagent.
This category was created to provide a "home" for inorganic compounds (such as NaBH 4) that are widely used in stoichiometric quantities in organic chemistry, but widely used organic reagents (such as oxalyl chloride) may belong here also.
2,2-Dimethoxypropane (DMP) is an organic compound with the formula (CH 3) 2 C(OCH 3) 2. A colorless liquid, it is the product of the condensation of acetone and methanol. DMP is used as a water scavenger in water-sensitive reactions. Upon acid-catalyzed reaction, DMP reacts quantitatively with water to form acetone and methanol. [2]
MOP (2-methoxy-2-propyl) p-Toluenesulfonic acid and 2-methoxypropene: tetrabutylammonium fluoride (1 mol eq., THF, -1 °C, 6 h) The hydroxyl group in hydroxyester 24 (Scheme 3) was protected as a MOP ether in order to decarboxylate the β-ketoester group. TBS (tert-butyldimethylsilyl) butyllithium, tetrahydrofuran, tert-butyldimethylsilyl chloride
The taxol synthesis started from the terpene verbenone 1 in Scheme 1, which is the oxidation product of naturally occurring α-pinene and forming ring A. Construction of ring B started with abstraction of the pendant methyl group proton by potassium tert-butoxide (conjugated anion is formed) followed by nucleophilic displacement of the bromine atom in prenyl bromide 2 to form diene 3.
The reaction mechanism of the Mitsunobu reaction is fairly complex. The identity of intermediates and the roles they play has been the subject of debate. Initially, the triphenyl phosphine (2) makes a nucleophilic attack upon diethyl azodicarboxylate (1) producing a betaine intermediate 3, which deprotonates the carboxylic acid (4) to form the ion pair 5.
The Seyferth–Gilbert homologation is a chemical reaction of an aryl ketone 1 (or aldehyde) with dimethyl (diazomethyl)phosphonate 2 and potassium tert-butoxide to give substituted alkynes 3. [1] [2] Dimethyl (diazomethyl)phosphonate 2 is often called the Seyferth–Gilbert reagent. [3] The Seyferth–Gilbert homologation
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