(E)-But-2-enoic acid (1R,2S,4R)-2-benzyl-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester

Base Information

• Chemical Name: (E)-But-2-enoic acid (1R,2S,4R)-2-benzyl-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester
• CAS No.: 105999-95-9
• Molecular Formula: C₂₁H₂₈O₂
• Molecular Weight: 312.452

Synonyms:(E)-But-2-enoic acid (1R,2S,4R)-2-benzyl-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester

Chemical Property of (E)-But-2-enoic acid (1R,2S,4R)-2-benzyl-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester

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Technology Process of (E)-But-2-enoic acid (1R,2S,4R)-2-benzyl-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester

There total 3 articles about (E)-But-2-enoic acid (1R,2S,4R)-2-benzyl-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester 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: 68.0%

(1R,2S,4R)-2-Benzyl-1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-ol (106037-19-8) + crotonyl chloride (10487-71-5) → (E)-But-2-enoic acid (1R,2S,4R)-2-benzyl-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester (105999-95-9)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; 1.) rt., 45 min; 2.) reflux, 6h;

DOI:10.1016/S0040-4020(01)91437-1

Reference yield:

(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one (464-49-3,68546-28-1) → (E)-But-2-enoic acid (1R,2S,4R)-2-benzyl-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester (105999-95-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 69 percent / 1.) magnesium / tetrahydrofuran / 24 h / Heating

2: 68 percent / BuLi / tetrahydrofuran / 1.) rt., 45 min; 2.) reflux, 6h

With n-butyllithium; magnesium; In tetrahydrofuran;

DOI:10.1016/S0040-4020(01)91437-1

Reference yield:

benzyl bromide (100-39-0) → (E)-But-2-enoic acid (1R,2S,4R)-2-benzyl-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester (105999-95-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 69 percent / 1.) magnesium / tetrahydrofuran / 24 h / Heating

2: 68 percent / BuLi / tetrahydrofuran / 1.) rt., 45 min; 2.) reflux, 6h

With n-butyllithium; magnesium; In tetrahydrofuran;

DOI:10.1016/S0040-4020(01)91437-1

upstream raw materials:

(1R,2S,4R)-2-Benzyl-1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-ol

crotonyl chloride

(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one

benzyl bromide

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