2-((carbomethoxy)methylidene)-5-(3-(benzyloxy)oct-1-en-1-yl)tetrahydrofuran

Base Information

Chemical Name:2-((carbomethoxy)methylidene)-5-(3-(benzyloxy)oct-1-en-1-yl)tetrahydrofuran
CAS No.:74275-68-6
Molecular Formula:C₂₂H₃₀O₄
Molecular Weight:358.478
Hs Code.:

Synonyms:2-((carbomethoxy)methylidene)-5-(3-(benzyloxy)oct-1-en-1-yl)tetrahydrofuran

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Chemical Property of 2-((carbomethoxy)methylidene)-5-(3-(benzyloxy)oct-1-en-1-yl)tetrahydrofuran

Chemical Property:

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Technology Process of 2-((carbomethoxy)methylidene)-5-(3-(benzyloxy)oct-1-en-1-yl)tetrahydrofuran

There total 13 articles about 2-((carbomethoxy)methylidene)-5-(3-(benzyloxy)oct-1-en-1-yl)tetrahydrofuran 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: 45.0%

: 76042-80-3
methyl 9-(benzyloxy)-8-hydroxy-6(E,Z)-en-3-oxotetradecanoate

: 74275-68-6
2-((carbomethoxy)methylidene)-5-(3-(benzyloxy)oct-1-en-1-yl)tetrahydrofuran

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; 1.) -78 deg C, 1 h, 2.) 0 deg C, 2 h;
DOI:10.1021/ja00547a015

Reference yield:

: [1-(1-Ethoxy-vinyl)-hexyloxymethyl]-benzene

: 74275-68-6
2-((carbomethoxy)methylidene)-5-(3-(benzyloxy)oct-1-en-1-yl)tetrahydrofuran

Guidance literature:: Multi-step reaction with 10 steps

1: 63 percent / 0.5 M hydrochloric acid / tetrahydrofuran / 24 h

2: 70 percent / lithium diisopropylamide / tetrahydrofuran / -78 °C

3: 1.) phosphorus oxychloride, HMPA, 2.) pyridine / 1.) room temperature -> 50 deg C, 2.) 50 deg C -> 100 deg C

4: 73 percent / DIBAL-H, n-butyllithium / tetrahydrofuran; hexane / -78 °C

5: 1.83 g / 48percent fluoboric acid / diethyl ether

6: 85 percent / lithium diisopropyl amide / diethyl ether / -78 °C

7: MCPBA / CH₂Cl₂ / 12 h / Ambient temperature

8: magnesium methoxide / methanol / Ambient temperature

9: 150 mg / 4-(dimethylamino)pyridine / CH₂Cl₂ / 1.5 h / Ambient temperature

10: 1.) sodium hydride / 2.) tetrakis(triphenylphosphine)palladium / 1.) THF, room temperature, 45 min, 2.) reflux, 4.5 h

With pyridine; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; tetrafluoroboric acid; n-butyllithium; sodium hydride; diisobutylaluminium hydride; magnesium methanolate; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; trichlorophosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane;
DOI:10.1021/ja00547a015

Reference yield:

: 66-25-1
hexanal

: 74275-68-6
2-((carbomethoxy)methylidene)-5-(3-(benzyloxy)oct-1-en-1-yl)tetrahydrofuran

Guidance literature:: Multi-step reaction with 11 steps

1: 2.) HMPA / 1.) THF, -78 deg C, 20 min, 2.) reflux, overnight

2: 63 percent / 0.5 M hydrochloric acid / tetrahydrofuran / 24 h

3: 70 percent / lithium diisopropylamide / tetrahydrofuran / -78 °C

4: 1.) phosphorus oxychloride, HMPA, 2.) pyridine / 1.) room temperature -> 50 deg C, 2.) 50 deg C -> 100 deg C

5: 73 percent / DIBAL-H, n-butyllithium / tetrahydrofuran; hexane / -78 °C

6: 1.83 g / 48percent fluoboric acid / diethyl ether

7: 85 percent / lithium diisopropyl amide / diethyl ether / -78 °C

8: MCPBA / CH₂Cl₂ / 12 h / Ambient temperature

9: magnesium methoxide / methanol / Ambient temperature

10: 150 mg / 4-(dimethylamino)pyridine / CH₂Cl₂ / 1.5 h / Ambient temperature

11: 1.) sodium hydride / 2.) tetrakis(triphenylphosphine)palladium / 1.) THF, room temperature, 45 min, 2.) reflux, 4.5 h

With pyridine; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; tetrafluoroboric acid; n-butyllithium; sodium hydride; diisobutylaluminium hydride; magnesium methanolate; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; trichlorophosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane;
DOI:10.1021/ja00547a015