(E)-2-methyl-5-<(1α,6α,7α)-3-<(benzyloxy)methyl>-7-methylbicyclo<4.1.0>hept-2-en-7-yl>-2-penten-1-ol

Base Information

Chemical Name:(E)-2-methyl-5-<(1α,6α,7α)-3-<(benzyloxy)methyl>-7-methylbicyclo<4.1.0>hept-2-en-7-yl>-2-penten-1-ol
CAS No.:116150-19-7
Molecular Formula:C₂₂H₃₀O₂
Molecular Weight:326.479
Hs Code.:

Synonyms:(E)-2-methyl-5-<(1α,6α,7α)-3-<(benzyloxy)methyl>-7-methylbicyclo<4.1.0>hept-2-en-7-yl>-2-penten-1-ol

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Chemical Property of (E)-2-methyl-5-<(1α,6α,7α)-3-<(benzyloxy)methyl>-7-methylbicyclo<4.1.0>hept-2-en-7-yl>-2-penten-1-ol

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Technology Process of (E)-2-methyl-5-<(1α,6α,7α)-3-<(benzyloxy)methyl>-7-methylbicyclo<4.1.0>hept-2-en-7-yl>-2-penten-1-ol

There total 12 articles about (E)-2-methyl-5-<(1α,6α,7α)-3-<(benzyloxy)methyl>-7-methylbicyclo<4.1.0>hept-2-en-7-yl>-2-penten-1-ol 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: 92.0%

: 116150-18-6,116261-22-4
ethyl (E)-2-methyl-5-<(1α,6α,7α)-3-<(benzyloxy)methyl>-7-methylbicyclo<4.1.0>hept-2-en-7-yl>-2-pentenoate

: 116150-19-7
(E)-2-methyl-5-<(1α,6α,7α)-3-<(benzyloxy)methyl>-7-methylbicyclo<4.1.0>hept-2-en-7-yl>-2-penten-1-ol

Guidance literature:: With diisobutylaluminium hydride; In diethyl ether; hexane; at 0 ℃; for 1h;
DOI:10.1021/jo00255a045

Reference yield:

: 3725-40-4
ethyl 1,3-cyclohexadiene-1-carboxylate

: 116150-19-7
(E)-2-methyl-5-<(1α,6α,7α)-3-<(benzyloxy)methyl>-7-methylbicyclo<4.1.0>hept-2-en-7-yl>-2-penten-1-ol

Guidance literature:: Multi-step reaction with 12 steps

1: 86 percent / AlCl₃, LiAlH₄ / diethyl ether / 17 h / 0 - 20 °C

2: 1.) NaH, EtOH / 1.) THF, reflux, 2 h, 2.) RT, 11 h

3: 63 percent / Et₃N / pentane / 16 h

4: 53 percent / AgNO₃ / 47 h / Heating

5: 95 percent / LiAlH₄ / diethyl ether / 4 h / Ambient temperature

6: 65 percent / pyridinium chlorochromate, celite / CH₂Cl₂ / 5 h / Ambient temperature

7: 1.) NaH / 1.) ether, reflux, 10 min, 2.) reflux, 10 min

8: 63 percent / CuI, MeLi, DIBAL-H / hexamethylphosphoric acid triamide; tetrahydrofuran; hexane / 9 h / -55 - -45 °C

9: 97 percent / LiAlH₄ / diethyl ether / 3 h / Ambient temperature

10: 89 percent / pyridinium chlorochromate, celite / CH₂Cl₂ / 5 h / Ambient temperature

11: 1.) NaH / 1.) ether, reflux, 10 min, 2.) reflux, 10 min

12: 92 percent / diisobutylaluminum hydride (DIBAL-H) / hexane; diethyl ether / 1 h / 0 °C

With copper(l) iodide; lithium aluminium tetrahydride; aluminium trichloride; ethanol; Celite; methyllithium; sodium hydride; diisobutylaluminium hydride; silver nitrate; triethylamine; pyridinium chlorochromate; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; dichloromethane; pentane;
DOI:10.1021/jo00255a045

Reference yield:

: 21203-48-5
1,3-cyclohexadiene-1-methanol

: 116150-19-7
(E)-2-methyl-5-<(1α,6α,7α)-3-<(benzyloxy)methyl>-7-methylbicyclo<4.1.0>hept-2-en-7-yl>-2-penten-1-ol

Guidance literature:: Multi-step reaction with 11 steps

1: 1.) NaH, EtOH / 1.) THF, reflux, 2 h, 2.) RT, 11 h

2: 63 percent / Et₃N / pentane / 16 h

3: 53 percent / AgNO₃ / 47 h / Heating

4: 95 percent / LiAlH₄ / diethyl ether / 4 h / Ambient temperature

5: 65 percent / pyridinium chlorochromate, celite / CH₂Cl₂ / 5 h / Ambient temperature

6: 1.) NaH / 1.) ether, reflux, 10 min, 2.) reflux, 10 min

7: 63 percent / CuI, MeLi, DIBAL-H / hexamethylphosphoric acid triamide; tetrahydrofuran; hexane / 9 h / -55 - -45 °C

8: 97 percent / LiAlH₄ / diethyl ether / 3 h / Ambient temperature

9: 89 percent / pyridinium chlorochromate, celite / CH₂Cl₂ / 5 h / Ambient temperature

10: 1.) NaH / 1.) ether, reflux, 10 min, 2.) reflux, 10 min

11: 92 percent / diisobutylaluminum hydride (DIBAL-H) / hexane; diethyl ether / 1 h / 0 °C

With copper(l) iodide; lithium aluminium tetrahydride; ethanol; Celite; methyllithium; sodium hydride; diisobutylaluminium hydride; silver nitrate; triethylamine; pyridinium chlorochromate; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; dichloromethane; pentane;
DOI:10.1021/jo00255a045