ethyl cinnamate-3-d

Base Information

• Chemical Name: ethyl cinnamate-3-d
• CAS No.: 87482-94-8
• Molecular Formula: C₁₁H₁₂O₂
• Molecular Weight: 177.207
• Mol file: 87482-94-8.mol

Synonyms:ethyl cinnamate-3-d

Chemical Property of ethyl cinnamate-3-d

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

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Technology Process of ethyl cinnamate-3-d

There total 10 articles about ethyl cinnamate-3-d which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 53.8%

Benzaldehyde-d (3592-47-0) + ethyl 2-(dimethoxyphosphoryl)acetate (311-46-6) → ethyl cinnamate-3-d (87482-94-8)

Guidance literature:

With sodium hydride; In tert-butyl alcohol; 1.) 0 deg C, 30 min, 2.) reflux, 2 h;

DOI:10.1021/jo00172a012

Reference yield:

ethyl 2-bromo-3-phenylpropionate (101308-40-1,129592-91-2,101308-42-3,39149-82-1) → ethyl 3-phenyl-2-propenoate (103-36-6) + ethyl cinnamate-3-d (87482-94-8)

Guidance literature:

With tetraethylammonium bromide; In acetonitrile; at 66.9 ℃; Mechanism; var. temp., var. solv., var. source of Br^(1-), with ethyl 2-bromo-3-phenylpropionate-3,3-d2; prim. isotope effect, effect of substituents;

DOI:10.1021/jo00172a012

Reference yield:

methyl 2-bromo-2-methyl-3-phenylpropionate-3-d (79722-34-2) → ethyl 3-phenyl-2-propenoate (103-36-6) + ethyl cinnamate-3-d (87482-94-8)

Guidance literature:

With lithium bromide; In N,N-dimethyl-formamide; at 66.3 ℃; Mechanism; var. temp., var. solv. var source of Br^(1-), with methyl 2-bromo-2-methyl-3-phenylpropionate-3,3-d2; inter- and intramolecular kinetic isotope effect;

DOI:10.1021/jo00172a012

upstream raw materials:

Benzaldehyde-d

ethyl 2-(dimethoxyphosphoryl)acetate

ethyl 2-bromo-3-phenylpropionate

methyl 2-bromo-2-methyl-3-phenylpropionate-3-d

Downstream raw materials:

trans-<β-2H>cinnamaldehyde

(E)-1-(benzo[d][1,3]dioxol-6-yl)-3-(dimethyl(phenyl)silyl)prop-2-en-1-ol

Refernces

• 1、 Ryan, Sarah J.,Stasch, Andreas,Paddon-Row, Michael N.,Lupton, David W.. "Synthetic and quantum mechanical studies into the N- heterocyclic carbene catalyzed (4 + 2) cycloaddition". experimental part. p. 1113 - 1124. Retrieved 2012/03/10.
• 2、 Kwart, Harold,Gaffney, Anne. "Bromide Ion Promoted β-Elimination in α-Bromo Ester Substrates. Evidence for an Intermediate in the E2C Reaction". . p. 4502 - 4508. Retrieved 2007/10/02.