ethyl 6'-allyl-4',5',6',6'a-tetrahydro-5',5'-dimethylspiro<1,3-dioxolane-2,2'(1'H)-pentalene>-3'carboxylate

Base Information

Chemical Name:ethyl 6'-allyl-4',5',6',6'a-tetrahydro-5',5'-dimethylspiro<1,3-dioxolane-2,2'(1'H)-pentalene>-3'carboxylate
CAS No.:83588-28-7
Molecular Formula:C₁₈H₂₆O₄
Molecular Weight:306.402
Hs Code.:

Synonyms:ethyl 6'-allyl-4',5',6',6'a-tetrahydro-5',5'-dimethylspiro<1,3-dioxolane-2,2'(1'H)-pentalene>-3'carboxylate

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Chemical Property of ethyl 6'-allyl-4',5',6',6'a-tetrahydro-5',5'-dimethylspiro<1,3-dioxolane-2,2'(1'H)-pentalene>-3'carboxylate

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Technology Process of ethyl 6'-allyl-4',5',6',6'a-tetrahydro-5',5'-dimethylspiro<1,3-dioxolane-2,2'(1'H)-pentalene>-3'carboxylate

There total 1 articles about ethyl 6'-allyl-4',5',6',6'a-tetrahydro-5',5'-dimethylspiro<1,3-dioxolane-2,2'(1'H)-pentalene>-3'carboxylate 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:

: 22748-16-9
4,4-dimethylcyclopent-2-ene-1-one

: 83588-28-7
ethyl 6'-allyl-4',5',6',6'a-tetrahydro-5',5'-dimethylspiro<1,3-dioxolane-2,2'(1'H)-pentalene>-3'carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) Rieke magnesium, cuprous bromide-dimethyl sulfide, 2.) Et₃N / 1.) THF, ether, -78 deg C, 2.) -78 deg C -> 5 deg C

2: 1.) LiNH₂, 2.) perchloric acid / 1.) liquid ammonia, THF, -33 deg C, 6 min 2.) CCl₂H₂, 2 h

3: 75 percent / sodium ethoxide / ethanol / 2 h / Ambient temperature

4: 99 percent / p-TsOH / benzene / 4 h / Heating

With perchloric acid; lithium amide; copper(I) bromide dimethylsulfide complex; sodium ethanolate; toluene-4-sulfonic acid; magnesium; triethylamine; In ethanol; benzene;
DOI:10.1021/ja00388a029

Reference yield:

: 83588-28-7
ethyl 6'-allyl-4',5',6',6'a-tetrahydro-5',5'-dimethylspiro<1,3-dioxolane-2,2'(1'H)-pentalene>-3'carboxylate

: 83588-35-6
5-(benzyloxy)octahydro-7-(2-hydroxyethyl)-8,8-dimethylpentaleno<1,6a-c>pyran-2(1H)-one p-toluenesulfonate

Guidance literature:: Multi-step reaction with 9 steps

1: 68 percent / diisobutylaluminum hydride / diethyl ether; hexane / -116 deg C, 2 h -> -50 deg C

2: 90 percent / mercuric acetate / 6 h / Heating

3: 56 percent / decahydronaphthalene / 4 h / 155 °C

4: 91 percent / pyridinium tosylate / acetone / 0.25 h / Heating

5: 1.) NaOH, 2.) Jones reagent / 1.) THF, water, 1 h, 2.) acetone, 0 deg C, 30 min

6: 1.) tert-butylamine-borane, 2.) HCl, 3.) collidine, trifluoromethanesulfonic anhydride

7: 1.) ozone, 2.) dimethyl sulfide / 1.) methanol, -78 deg C, 5 min, 2.) -12 deg C

8: 1.) tert-butylamine-borane, 2.) HCl / 1.) THF, 0 deg C, 30 min

9: 83 percent / 4-dimethylaminopyridine, Et₃N / CH₂Cl₂ / 0 °C

With 2,3,5-trimethyl-pyridine; hydrogenchloride; dmap; sodium hydroxide; jones reagent; dimethylsulfide; mercury(II) diacetate; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; borane tert-butylamine; ozone; trifluoromethanesulfonic acid anhydride; triethylamine; In diethyl ether; hexane; dichloromethane; acetone; decalin;
DOI:10.1021/ja00388a029

Reference yield:

: 83588-28-7
ethyl 6'-allyl-4',5',6',6'a-tetrahydro-5',5'-dimethylspiro<1,3-dioxolane-2,2'(1'H)-pentalene>-3'carboxylate

: 78217-46-6
7-allyl-5-(benzyloxy)octahydro-8,8-dimethylpentaleno<1,6a-c>pyran-2(1H)-one

Guidance literature:: Multi-step reaction with 6 steps

1: 68 percent / diisobutylaluminum hydride / diethyl ether; hexane / -116 deg C, 2 h -> -50 deg C

2: 90 percent / mercuric acetate / 6 h / Heating

3: 56 percent / decahydronaphthalene / 4 h / 155 °C

4: 91 percent / pyridinium tosylate / acetone / 0.25 h / Heating

5: 1.) NaOH, 2.) Jones reagent / 1.) THF, water, 1 h, 2.) acetone, 0 deg C, 30 min

6: 1.) tert-butylamine-borane, 2.) HCl, 3.) collidine, trifluoromethanesulfonic anhydride

With 2,3,5-trimethyl-pyridine; hydrogenchloride; sodium hydroxide; jones reagent; mercury(II) diacetate; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; borane tert-butylamine; trifluoromethanesulfonic acid anhydride; In diethyl ether; hexane; acetone; decalin;
DOI:10.1021/ja00388a029