2-Propenoic acid, 3-[(2R)-2,3-dihydro-2-(4-phenylbutyl)-4-benzofuranyl]-, (2E)-

Base Information

• Chemical Name: 2-Propenoic acid, 3-[(2R)-2,3-dihydro-2-(4-phenylbutyl)-4-benzofuranyl]-, (2E)-
• CAS No.: 532400-22-9
• Molecular Formula: C₂₁H₂₂O₃
• Molecular Weight: 322.404

Synonyms:

Chemical Property of 2-Propenoic acid, 3-[(2R)-2,3-dihydro-2-(4-phenylbutyl)-4-benzofuranyl]-, (2E)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-Propenoic acid, 3-[(2R)-2,3-dihydro-2-(4-phenylbutyl)-4-benzofuranyl]-, (2E)-

There total 12 articles about 2-Propenoic acid, 3-[(2R)-2,3-dihydro-2-(4-phenylbutyl)-4-benzofuranyl]-, (2E)- 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:

2-allyl-3-hydroxybenzoic acid ethyl ester (53596-59-1) → (E)-3-[(R)-2-(4-Phenyl-butyl)-2,3-dihydro-benzofuran-4-yl]-acrylic acid (532400-22-9)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 96 percent / i-Pr₂NEt / CH₂Cl₂ / 20 °C

2.1: 74 percent / OsO₄; aq. NaIO₄ / ethyl acetate / 20 °C

3.1: (-)-B-methoxydisopinocampheylborane / diethyl ether

4.1: BH₃ / tetrahydrofuran

4.2: 75 percent / aq. H₂O₂; NaOH / tetrahydrofuran

5.1: 90 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂

6.1: 86 percent / n-BuLi / tetrahydrofuran

7.1: 99 percent / H₂ / Pd/C / ethyl acetate

8.1: 99 percent / DIBAL-H / toluene / -78 °C

9.1: 98 percent / tetrahydrofuran / Heating

10.1: 100 percent / HCl / ethanol / 20 °C

11.1: 95 percent / Ph₃P; diethyl azodicarboxylate / tetrahydrofuran / 0 - 25 °C

12.1: 96 percent / aq. NaOH / methanol / Heating

With hydrogenchloride; sodium hydroxide; sodium periodate; osmium(VIII) oxide; n-butyllithium; oxalyl dichloride; borane; hydrogen; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; (-)-B-methoxydiisopinocampheylborane; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; ethyl acetate; toluene; 5.1: Swern oxidation / 6.1: Wittig reaction / 9.1: Wittig reaction / 11.1: Mitsunobu reaction;

DOI:10.1016/j.bmcl.2005.01.015

Reference yield:

benzyltriphenylphosphonium bromide (1449-46-3) → (E)-3-[(R)-2-(4-Phenyl-butyl)-2,3-dihydro-benzofuran-4-yl]-acrylic acid (532400-22-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 86 percent / n-BuLi / tetrahydrofuran

2: 99 percent / H₂ / Pd/C / ethyl acetate

3: 99 percent / DIBAL-H / toluene / -78 °C

4: 98 percent / tetrahydrofuran / Heating

5: 100 percent / HCl / ethanol / 20 °C

6: 95 percent / Ph₃P; diethyl azodicarboxylate / tetrahydrofuran / 0 - 25 °C

7: 96 percent / aq. NaOH / methanol / Heating

With hydrogenchloride; sodium hydroxide; n-butyllithium; hydrogen; diisobutylaluminium hydride; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; ethyl acetate; toluene; 1: Wittig reaction / 4: Wittig reaction / 6: Mitsunobu reaction;

DOI:10.1016/j.bmcl.2005.01.015

Reference yield:

ethyl 3-(Methoxymethoxy)-2-(2-oxoethyl)benzoate (532399-60-3) → (E)-3-[(R)-2-(4-Phenyl-butyl)-2,3-dihydro-benzofuran-4-yl]-acrylic acid (532400-22-9)

Guidance literature:

Multi-step reaction with 10 steps

1.1: (-)-B-methoxydisopinocampheylborane / diethyl ether

2.1: BH₃ / tetrahydrofuran

2.2: 75 percent / aq. H₂O₂; NaOH / tetrahydrofuran

3.1: 90 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂

4.1: 86 percent / n-BuLi / tetrahydrofuran

5.1: 99 percent / H₂ / Pd/C / ethyl acetate

6.1: 99 percent / DIBAL-H / toluene / -78 °C

7.1: 98 percent / tetrahydrofuran / Heating

8.1: 100 percent / HCl / ethanol / 20 °C

9.1: 95 percent / Ph₃P; diethyl azodicarboxylate / tetrahydrofuran / 0 - 25 °C

10.1: 96 percent / aq. NaOH / methanol / Heating

With hydrogenchloride; sodium hydroxide; n-butyllithium; oxalyl dichloride; borane; hydrogen; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; (-)-B-methoxydiisopinocampheylborane; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; ethyl acetate; toluene; 3.1: Swern oxidation / 4.1: Wittig reaction / 7.1: Wittig reaction / 9.1: Mitsunobu reaction;

DOI:10.1016/j.bmcl.2005.01.015

upstream raw materials:

2-allyl-3-hydroxybenzoic acid ethyl ester

benzyltriphenylphosphonium bromide

ethyl 3-(Methoxymethoxy)-2-(2-oxoethyl)benzoate

ethyl 3-(Methoxymethoxy)-2-prop-2-enylbenzoate

Downstream raw materials:

((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-{(1R,2R)-2-[(R)-2-(4-phenyl-butyl)-2,3-dihydro-benzofuran-4-yl]-cyclopropyl}-methanone

(E)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-[(R)-2-(4-phenyl-butyl)-2,3-dihydro-benzofuran-4-yl]-propenone

1-Ethyl-3-{(1R,2R)-2-[(R)-2-(4-phenyl-butyl)-2,3-dihydro-benzofuran-4-yl]-cyclopropylmethyl}-urea

{(1R,2R)-2-[(R)-2-(4-Phenyl-butyl)-2,3-dihydro-benzofuran-4-yl]-cyclopropyl}-methanol

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