4α-(benzyloxy)-1α-ethenyl-2α-<2-(4-methoxybenzocyclobutenyl)-2-(benzyloxy)ethyl>-1β-methylcyclohexane

Base Information

• Chemical Name: 4α-(benzyloxy)-1α-ethenyl-2α-<2-(4-methoxybenzocyclobutenyl)-2-(benzyloxy)ethyl>-1β-methylcyclohexane
• CAS No.: 81277-68-1
• Molecular Formula: C₃₄H₄₀O₃
• Molecular Weight: 496.69

Synonyms:4α-(benzyloxy)-1α-ethenyl-2α-<2-(4-methoxybenzocyclobutenyl)-2-(benzyloxy)ethyl>-1β-methylcyclohexane

Chemical Property of 4α-(benzyloxy)-1α-ethenyl-2α-<2-(4-methoxybenzocyclobutenyl)-2-(benzyloxy)ethyl>-1β-methylcyclohexane

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of 4α-(benzyloxy)-1α-ethenyl-2α-<2-(4-methoxybenzocyclobutenyl)-2-(benzyloxy)ethyl>-1β-methylcyclohexane

There total 20 articles about 4α-(benzyloxy)-1α-ethenyl-2α-<2-(4-methoxybenzocyclobutenyl)-2-(benzyloxy)ethyl>-1β-methylcyclohexane 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: 81.0%

benzyl bromide (100-39-0) + 1α-ethenyl-4α-hydroxy-2α-<2-(4-methoxybenzocyclobutenyl)-2-hydroxyethyl>-1β-methylcyclohexane (73230-88-3) → 4α-(benzyloxy)-1α-ethenyl-2α-<2-(4-methoxybenzocyclobutenyl)-2-(benzyloxy)ethyl>-1β-methylcyclohexane (81277-68-1)

Guidance literature:

With sodium hydride; In tetrahydrofuran; for 16h; Heating;

DOI:10.1021/jo00133a020

Reference yield:

(8aS)-1,1-(1,2-ethylenedioxy)-1,2,3,4,6,7,8,8a-octahydro-8a-methyl-6-oxonaphthalene (61950-54-7) → 4α-(benzyloxy)-1α-ethenyl-2α-<2-(4-methoxybenzocyclobutenyl)-2-(benzyloxy)ethyl>-1β-methylcyclohexane (81277-68-1)

Guidance literature:

Multi-step reaction with 20 steps

1: 89 percent / H₂ / 10percent palladium on carbon / aq. ethanol / 6 h / 760 Torr / Ambient temperature

2: 79 percent / sodium borohydride / methanol / 1 h / 0 °C

3: 85 percent / pyridine / 16 h / Ambient temperature

4: 96 percent / 5percent aq. hydrochloric acid / acetone / 16 h / Ambient temperature

5: bromine / CHCl₃ / 2 h / 0 °C

6: 97 percent / lithium bromide, lithium carbonate / dimethylformamide / 3.5 h / 125 - 130 °C

7: 1.) sodium amide, 2.) 5percent aq. potassium hydroxide / 1.) ammonia (liquid)/THF, -78 deg C, 2 h, 2.) methanol, room temp., 2 h

8: 90 percent / p-toluenesulfonic acid / benzene / 3 h / Heating

9: 96 percent / sodium / liquid ammonia; tetrahydrofuran; ethanol / 2 h / -78 °C

10: 99 percent / 5percent aq. hydrochloric acid / acetone / 16 h / Ambient temperature

11: pyridinium hydrobromide perbromide / CHCl₃ / 1 h / Ambient temperature

12: 96 percent / lithium bromide, lithium carbonate / dimethylformamide / 14 h / 45 °C

13: 77 percent / 30percent hydrogen peroxide, 10percent aq. sodium hydroxide / methanol / 6 h / Ambient temperature

14: 100 percent / p-toluenesulfonic acid / CH₂Cl₂ / 4 h / Ambient temperature

15: 77 percent / lithium aluminum hydride / tetrahydrofuran / 15 h / Ambient temperature

16: 85 percent / 4-(dimethylamino)pyridine / pyridine / 16 h / Ambient temperature

17: 91 percent / sodium hydride / tetrahydrofuran / 14 h / Heating

18: 97 percent / p-toluenesulfonic acid / CH₂Cl₂ / 1 h / Ambient temperature

19: 58 percent / lithium aluminum hydride / tetrahydrofuran / 5 h / Ambient temperature

20: 81 percent / sodium hydride / tetrahydrofuran / 16 h / Heating

With hydrogenchloride; dmap; potassium hydroxide; sodium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; hydrogen; dihydrogen peroxide; bromine; pyridinium hydrobromide perbromide; sodium; lithium carbonate; sodium hydride; toluene-4-sulfonic acid; sodium amide; lithium bromide; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; chloroform; ammonia; N,N-dimethyl-formamide; acetone; benzene;

DOI:10.1021/jo00133a020

Reference yield:

(+)-(4aR,8aS)-1,2,3,4,4aβ,5,6,7,8,8a-decahydro-1,1-(1,2-ethylenedioxy)-8aβ-methyl-6-oxonaphthalene (81339-52-8) → 4α-(benzyloxy)-1α-ethenyl-2α-<2-(4-methoxybenzocyclobutenyl)-2-(benzyloxy)ethyl>-1β-methylcyclohexane (81277-68-1)

Guidance literature:

Multi-step reaction with 19 steps

1: 79 percent / sodium borohydride / methanol / 1 h / 0 °C

2: 85 percent / pyridine / 16 h / Ambient temperature

3: 96 percent / 5percent aq. hydrochloric acid / acetone / 16 h / Ambient temperature

4: bromine / CHCl₃ / 2 h / 0 °C

5: 97 percent / lithium bromide, lithium carbonate / dimethylformamide / 3.5 h / 125 - 130 °C

6: 1.) sodium amide, 2.) 5percent aq. potassium hydroxide / 1.) ammonia (liquid)/THF, -78 deg C, 2 h, 2.) methanol, room temp., 2 h

7: 90 percent / p-toluenesulfonic acid / benzene / 3 h / Heating

8: 96 percent / sodium / liquid ammonia; tetrahydrofuran; ethanol / 2 h / -78 °C

9: 99 percent / 5percent aq. hydrochloric acid / acetone / 16 h / Ambient temperature

10: pyridinium hydrobromide perbromide / CHCl₃ / 1 h / Ambient temperature

11: 96 percent / lithium bromide, lithium carbonate / dimethylformamide / 14 h / 45 °C

12: 77 percent / 30percent hydrogen peroxide, 10percent aq. sodium hydroxide / methanol / 6 h / Ambient temperature

13: 100 percent / p-toluenesulfonic acid / CH₂Cl₂ / 4 h / Ambient temperature

14: 77 percent / lithium aluminum hydride / tetrahydrofuran / 15 h / Ambient temperature

15: 85 percent / 4-(dimethylamino)pyridine / pyridine / 16 h / Ambient temperature

16: 91 percent / sodium hydride / tetrahydrofuran / 14 h / Heating

17: 97 percent / p-toluenesulfonic acid / CH₂Cl₂ / 1 h / Ambient temperature

18: 58 percent / lithium aluminum hydride / tetrahydrofuran / 5 h / Ambient temperature

19: 81 percent / sodium hydride / tetrahydrofuran / 16 h / Heating

With hydrogenchloride; dmap; potassium hydroxide; sodium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; dihydrogen peroxide; bromine; pyridinium hydrobromide perbromide; sodium; lithium carbonate; sodium hydride; toluene-4-sulfonic acid; sodium amide; lithium bromide; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; chloroform; ammonia; N,N-dimethyl-formamide; acetone; benzene;

DOI:10.1021/jo00133a020

upstream raw materials:

benzyl bromide

1α-ethenyl-4α-hydroxy-2α-<2-(4-methoxybenzocyclobutenyl)-2-hydroxyethyl>-1β-methylcyclohexane

(+)-(4aR,8aS)-1,2,3,4,4aβ,5,6,7,8,8a-decahydro-1,1-(1,2-ethylenedioxy)-8aβ-methyl-6-oxonaphthalene

(8aS)-1,1-(1,2-ethylenedioxy)-1,2,3,4,6,7,8,8a-octahydro-8a-methyl-6-oxonaphthalene

Downstream raw materials:

3α,7β-bis(benzyloxy)-17-methoxy-D-homo-18-nor-5β-androsta-13,15,17-triene

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