tert-butyl (2E)-5-methylhex-2-enoate

Base Information

• Chemical Name: tert-butyl (2E)-5-methylhex-2-enoate
• CAS No.: 138877-97-1
• Molecular Formula: C11H20O2
• Molecular Weight: 184.27500
• Mol file: 138877-97-1.mol

Synonyms:TERT-BUTYL (E)-3-OXO-4-HEXENOATE;tert-butyl (E)-3-oxohex-4-enoate;tert-Butyl (4E)-3-oxo-4-hexenoate;tert-butyl (E)-5-methyl-hex-2-enoate;(E)-tert-butyl 5-methyl-hex-2-enoate;

Chemical Property of tert-butyl (2E)-5-methylhex-2-enoate

Chemical Property:

• Vapor Pressure: 0.116mmHg at 25°C
• Boiling Point: 219.997oC at 760 mmHg
• Flash Point: 95.006oC
• PSA: 26.30000
• LogP: 2.93040

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of tert-butyl (2E)-5-methylhex-2-enoate

There total 5 articles about tert-butyl (2E)-5-methylhex-2-enoate 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: 96.0%

tert-butyl diethylphosphonoacetate (27784-76-5) + isovaleraldehyde (590-86-3) → tert-butyl (E)-5-methyl-hex-2-enoate (138877-97-1)

Guidance literature:

tert-butyl diethylphosphonoacetate; With methylmagnesium bromide; In tetrahydrofuran; diethyl ether; at 20 ℃; for 0.25h; Inert atmosphere;

isovaleraldehyde; In tetrahydrofuran; diethyl ether; diastereoselective reaction; Reflux; Inert atmosphere;

DOI:10.1021/ol802212e

Reference yield: 86.0%

bromoacetic acid tert-butyl ester (5292-43-3) + isovaleraldehyde (590-86-3) → tert-butyl (E)-5-methyl-hex-2-enoate (138877-97-1)

Guidance literature:

With triphenylphosphine; nanocrystalline aerogel prepared MgO; In N,N-dimethyl-formamide; at 20 ℃; for 11h;

DOI:10.1002/adsc.200606001

Reference yield: 69.0%

(E)-(3-methylbut-1-en-1-yl)boronic acid (70813-75-1) + (tert-Butoxycarbonylmethylene)triphenylphosphorane (86302-43-4,35000-38-5) → (E)-tert-butyl 5-methyl-4-oxohex-2-enoate + tert-butyl (E)-5-methyl-hex-2-enoate (138877-97-1)

Guidance literature:

With pyridine; water; oxygen; copper diacetate; In acetonitrile; at 30 ℃; for 11h; regioselective reaction;

DOI:10.1002/adsc.201701640

upstream raw materials:

bromoacetic acid tert-butyl ester

isovaleraldehyde

tert-butyl diethylphosphonoacetate

3-methyl-but-1-yne

Downstream raw materials:

tert-butyl (3S,αS)-3-(N-benzyl-N-α-methylbenzylamino)-5-methylhexanoate

tert-butyl (3R,αR)-3-(N-benzyl-N-α-methylbenzylamino)-5-methylhexanoate

(2R,3R,αR)-2-hydroxy-3-(N-benzyl-N-α-methylbenzylamino)-5-methylhexanol

(2R,αR)-2-(N-benzyl-N-α-methylbenzylamino)-4-methylpentanoic acid

Refernces

• 1、 Claridge, Timothy D. W.,Davies, Stephen G.,Lee, James A.,Nicholson, Rebecca L.,Roberts, Paul M.,Russell, Angela J.,Smith, Andrew D.,Toms, Steven M.. "Highly (E)-selective wadsworth-emmons reactions promoted by methylmagnesium bromide". supporting information; experimental part. p. 5437 - 5440. Retrieved 2009/06/18.
• 2、 Choudary, Boyapati M.,Mahendar, Koosam,Kantam, M. Lakshmi,Ranganath, Kalluri V. S.,Athar, Taimur. "The one-pot Wittig reaction: A facile synthesis of α,β- unsaturated esters and nitriles by using nanocrystalline magnesium oxide". . p. 1977 - 1985. Retrieved 2007/10/03.