40558-71-2

Upstream product

• 77772-22-6 Ethyl 2-(diphenylmethylsilyl)propionate 
• 100-44-7 benzyl chloride 
• 110366-33-1 3-Benzyl-3-hydroxy-2-methyl-4-phenyl-butyric acid 
• 92639-43-5 dimethyl (2-benzyl-2-hydroxy-1-methyl-3-phenyl)propylphosphonate 
• 110366-36-4 C₂₁H₂₄O₅ 
• 7623-09-8 2-chloropropionyl chloride 
• 1589-82-8 phenylmagnesium bromide 
• 102-04-5 1,3-Diphenylpropanone 

Relevant academic research and scientific papers

The Olefin Synthesis from β-Hydroxyalkylphosphonates Induced by Fluorides or Relatively Weak Bases

β-Hydroxyalkylphosphonates, which were prepared readily from alkylphosphonates and carbonyl compounds, were treated with a fluoride ion such as CsF or with relatively weak bases such as K2CO3 in N,N-dimethylformamide to give the corresponding olefins in good yields. One molar equivalent of water to bases is effective for increasing the yields of olefins. The stereochemistry of erythro-dimethyl (2-hydroxy-1-methyl-2-phenyl)ethylphosphonate was determined by X-ray crystallographic analysis. Use of threo-isomer gave (E)-olefin exclusively, while that of erythro-enricned isomer afforded predominantly (Z)-olefin, indicating that the present olefination proceeds stereospecifically in a manner of syn-elimination.

An Efficient Biogenetic-Type Transformation of 3-Tertiary-hydroxyalkanoic Acids to Olefinic Compounds

The readily available 3-tertiary-hydroxyalkanoic acids (3) could be smoothly converted to the olefinic compounds (5) by dehydrative decarboxylation, by treatment with N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline.This efficient reaction mimics the olefination at the initial stage of the so-called "mevalonic acid route".Keywords-olefination; biogenetic-type synthesis; β-hydroxyalkanoic acid; mevalonic acid route; dehydrative decarboxylation; β-propiolactone; mixed anhydride; acyl activation; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; 1-acyl-1H-imidazole

THE EFFECTIVENESS OF A WEAK BASE IN THE OLEFIN SYNTHESIS FROM β-HYDROXYALKYLPHOSPHONATES

β-Hydroxyalkylphosphonates were treated with a weak base such as potassium carbonate in N,N-dimethylformamide to give the corresponding olefins in good yields.

Direct and Regioselective Transformation of α-Chloro Carbonyl Compounds into Alkenes and Deuterioalkenes

The successive treatment ethyl chloroacetate or chloroacetyl chloride with Grignard reagents and lithium powder leads to symmetrical terminal olefins in a regioselective manner.The best results are obtained with acid chlorides.The influence of the temperature and the reaction time on overall yield of the process are studied; in general, yields are increased by working at low temperature (-60 deg C).Internally substituted olefins are obtained from α-chloro acid chlorides through a similar process.The treatment of α-chloro aldehydes, ketones and carboxylic acid derivatives (esters or acid chlorides) with lithium aluminium hydride or lithium aluminium hydride/aluminium chloride and lithium powder at low temperature (-60 deg C) leads in a regioselective manner to olefins with the same carbon skeleton as the starting carbonyl compound.Reactions with lithium aluminium deuteride lead to incorporation of deuterium at predetermined positions in the alkene.