(Z)-(R)-7-(2-fluoro-6-methoxy-4-pentylphenyl)-8-(methoxymethylene)-1,4-dioxaspiro[4.5]decane

Base Information

• Chemical Name: (Z)-(R)-7-(2-fluoro-6-methoxy-4-pentylphenyl)-8-(methoxymethylene)-1,4-dioxaspiro[4.5]decane
• CAS No.: 1421319-77-8
• Molecular Formula: C₂₂H₃₁FO₄
• Molecular Weight: 378.484
• Mol file: 1421319-77-8.mol

Synonyms:

Chemical Property of (Z)-(R)-7-(2-fluoro-6-methoxy-4-pentylphenyl)-8-(methoxymethylene)-1,4-dioxaspiro[4.5]decane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-(R)-7-(2-fluoro-6-methoxy-4-pentylphenyl)-8-(methoxymethylene)-1,4-dioxaspiro[4.5]decane

There total 9 articles about (Z)-(R)-7-(2-fluoro-6-methoxy-4-pentylphenyl)-8-(methoxymethylene)-1,4-dioxaspiro[4.5]decane 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:

(S)-7-(2-fluoro-6-methoxy-4-pentylphenyl)-1,4-dioxaspiro[4.5]decan-8-one (1421319-64-3) + (methoxymethyl)triphenylphosphonium chloride (4009-98-7) → (Z)-(R)-7-(2-fluoro-6-methoxy-4-pentylphenyl)-8-(methoxymethylene)-1,4-dioxaspiro[4.5]decane (1421319-77-8) + (E)-(R)-7-(2-fluoro-6-methoxy-4-pentylphenyl)-8-(methoxymethylene)-1,4-dioxaspiro[4.5]decane (1421319-68-7)

Guidance literature:

(methoxymethyl)triphenylphosphonium chloride; With n-butyllithium; In tetrahydrofuran; hexane; at 0 ℃; for 0.5h; Inert atmosphere;

(S)-7-(2-fluoro-6-methoxy-4-pentylphenyl)-1,4-dioxaspiro[4.5]decan-8-one; In tetrahydrofuran; at -78 - 20 ℃; for 2.3h; Overall yield = 90 %; Overall yield = 3.7 g; Inert atmosphere;

DOI:10.1021/ol303351y

Reference yield:

7-iodo-1,4-dioxaspiro[4.5]dec-6-en-8-one (1374219-14-3) → (Z)-(R)-7-(2-fluoro-6-methoxy-4-pentylphenyl)-8-(methoxymethylene)-1,4-dioxaspiro[4.5]decane (1421319-77-8) + (E)-(R)-7-(2-fluoro-6-methoxy-4-pentylphenyl)-8-(methoxymethylene)-1,4-dioxaspiro[4.5]decane (1421319-68-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; lithium chloride; sodium carbonate / water; 1,2-dimethoxyethane / 24 h / 80 °C / Inert atmosphere

2.1: hydrogen; 5%-palladium/activated carbon / ethanol / 12 h / 30 °C / Inert atmosphere

3.1: hydrogen; RuCl₂-(S)-SDP/(R,R)-DPEN; potassium tert-butylate / isopropyl alcohol / 12 h / 20 °C / 38002.6 Torr / Inert atmosphere; Glovebox

4.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.25 h / -78 °C / Inert atmosphere

4.2: 2 h / -10 °C / Inert atmosphere

5.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / 0 °C / Inert atmosphere

5.2: 2.3 h / -78 - 20 °C / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; oxalyl dichloride; 5%-palladium/activated carbon; RuCl₂-(S)-SDP/(R,R)-DPEN; potassium tert-butylate; hydrogen; sodium carbonate; dimethyl sulfoxide; lithium chloride; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; hexane; dichloromethane; water; isopropyl alcohol; 1.1: |Suzuki Coupling / 5.1: |Wittig Olefination;

DOI:10.1021/ol303351y

Reference yield:

n-pentylboronic acid (4737-50-2) → (Z)-(R)-7-(2-fluoro-6-methoxy-4-pentylphenyl)-8-(methoxymethylene)-1,4-dioxaspiro[4.5]decane (1421319-77-8) + (E)-(R)-7-(2-fluoro-6-methoxy-4-pentylphenyl)-8-(methoxymethylene)-1,4-dioxaspiro[4.5]decane (1421319-68-7)

Guidance literature:

Multi-step reaction with 7 steps

1.1: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; toluene / 6 h / 90 °C / Inert atmosphere

2.1: tert.-butyl lithium / tetrahydrofuran; pentane / 1 h / -78 °C / Inert atmosphere

2.2: 2 h / -78 - 20 °C / Inert atmosphere

3.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; lithium chloride; sodium carbonate / water; 1,2-dimethoxyethane / 24 h / 80 °C / Inert atmosphere

4.1: hydrogen; 5%-palladium/activated carbon / ethanol / 12 h / 30 °C / Inert atmosphere

5.1: hydrogen; RuCl₂-(S)-SDP/(R,R)-DPEN; potassium tert-butylate / isopropyl alcohol / 12 h / 20 °C / 38002.6 Torr / Inert atmosphere; Glovebox

6.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.25 h / -78 °C / Inert atmosphere

6.2: 2 h / -10 °C / Inert atmosphere

7.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / 0 °C / Inert atmosphere

7.2: 2.3 h / -78 - 20 °C / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; oxalyl dichloride; 5%-palladium/activated carbon; RuCl₂-(S)-SDP/(R,R)-DPEN; potassium tert-butylate; hydrogen; tert.-butyl lithium; sodium carbonate; potassium carbonate; dimethyl sulfoxide; lithium chloride; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; hexane; dichloromethane; water; isopropyl alcohol; toluene; pentane; 3.1: |Suzuki Coupling / 7.1: |Wittig Olefination;

DOI:10.1021/ol303351y

upstream raw materials:

1,4-dioxa-spiro[4.5]dec-6-en-8-one

7-iodo-1,4-dioxaspiro[4.5]dec-6-en-8-one

n-pentylboronic acid

7-(2-fluoro-6-methoxy-4-pentylphenyl)-1,4-dioxaspiro[4.5]dec-6-en-8-one